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Benzhydrylpiperazine

Benzhydrylpiperazine structure

CAS No:
841-77-0
Formula:
C17H20N2
Chemical Name:
Benzhydrylpiperazine
Synonyms:
Piperazine,1-(diphenylmethyl)-;1-(Diphenylmethyl)piperazine;Norcyclizine;Benzhydrylpiperazine;N-Benzhydrylpiperazine;1-Benzhydrylpiperazine;N-(Diphenylmethyl)piperazine;4-(Diphenylmethyl)piperazine;4-Benzhydrylpiperazine;NSC 35536
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

white to light yellow crystalline powder

Benzhydrylpiperazine Basic Attributes

Molecular Weight：

252.35

Exact Mass：

252.35

BRN：

222773

EC Number：

212-667-7

NSC Number：

35536

DSSTox ID：

DTXSID80232968

HScode：

2933599090

Characteristics

PSA：

15.3

XLogP3：

2.8

Appearance：

White to light yellow Crystalline Powder

Density：

1.1±0.1 g/cm3

Melting Point：

70-72 °C

Boiling Point：

189-190 °C @ Press: 1 Torr

Flash Point：

115 °C

Refractive Index：

1.584

Water Solubility：

H2O: 0.45 g/L (20 ºC)

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Safety Information

Packing level：

I; II; III

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

22-24/25

RTECS Number：

TL6465000

Marks：

Xn,Xi

Hazard note：

Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (96%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 51 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Metabolism/Metabolites：

1-Benzhydrylpiperazine is a known human metabolite of cinnarizine.

MeSH Entry Terms：

1-benzhydrylpiperazine

Benzhydrylpiperazine Use and Manufacturing

Methods of Manufacturing

Accurately weigh 10g of about 41 mmol of diphenylbromomethane, 9g about Piperazine 105mmol, 14g of about 101 mmol of K2CO3 and NaI. 6g 40mmol dissolved in about 85mL of toluene, stirred and dissolved, placed in an oil bath at 110 ° C the reaction was refluxed for 4h, TLC detection, after completion of the reaction, cooling, DCM was added and dispersed, the reaction system was filtered, residue discarded, the filtrate was collected, the filtrate was concentrated on silica gel column chromatography chromatography using elution system containing 1percent triethylamine, the volume of eluent of petroleum ether and ethyl acetate ratio of 1: 2-1: 3 gradient elution was carried out to give 7.6g of compound S8, yield 74.2percent.Solid potassium carbonate (0.56 g, 4.04 mmol) and catalytic NaI (0.12 g, 0.81 mmol) were added to a solution of piperazine (0.7 g, 8.1 mmol) in acetonitrile (15 mL) and stirred with heating until all the solids were dissolved. Bromodiphenylmethane 26 (1.0 g, 0.41 mmol) was added and the reaction mixture was heated at reflux at 90 °C for 8 hours. After completion of the reaction (TLC), the reaction was quenched with water (10 ml), extracted with ethyl acetate (2 × 15 ml), dried over anhydrous sodium sulphate and evaporated to afford crude yellow solid. The crude product was purified by column chromatography (2.5percent MeOH-DCM) to afford 27 (0.65 g, 65percent) as white solid. 1H-NMR (400 MHz, CDCl3): δ 7.35 (dd, J = 8.4 and 1.2 Hz, 4H), 7.19 (t, J = 7.6 Hz, 4H), 7.10 (tt, J = 7.6 and 1.2 Hz, 2H), 4.15 (s, 1H), 2.82 (t, J = 4.8 Hz, 4H), 2.30 (bs, 4H), 1.80 (bs, 1H).Compound, 2 (250 mg, 1.23 mmol) was taken in THF, and piperazinedihydrochloride (199 mg, 1.25 mmol) and KGeneral procedure: NaBH4 (0.6mol) was added to a stirred solution of benzophenones (1.0 mol)in methanol (2 vol) portionwise at room temperature for 45 min. The mixture was stirred for 2–3 h at ambient temperature (completion of reaction was monitoredby TLC), and was diluted with water (750 ml), acidified with acetic acid to pH 4, and extracted with dichloromethane (2x400 ml). The organic layer was washed with water (200 ml) and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to get pure benzhydrol derivatives as a white to off-white solid in 93–97percent yield. To the benzhydrol derivatives (1.0 mol) in toluene (370 ml) was added concentrated HCl (35percent in H2O, 370 ml) and tetrabutylammonium bromide(0.01 mol) at room temperature under stirring. Stirring was continued at 40–45 °C for 6–7 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. The organic layer was separated and concentrated under vacuum to obtain crude benzhydryl chloride derivatives as a light brown liquid in 95–97percent yield. To this benzhydryl chloride (0.96 mol) derivatives in toluene (380 ml) was added anhydrous piperazine (5.0 mol) at 60–70 °C for 45–60 min. The resulting mixture was heated under stirring at 90–100 °C for 8–10 h. The mixture was cooled after completion of the reaction. Water (380 ml) was added, and the organic layer was separated. The latter was washed with a 1:1 mixture of concentrated HCl/water(2x350 ml) and neutralized with 20percent NaOH solution (750 ml). The water layer was re-extracted into toluene (2x300 ml), dried over anhydrous sodium sulfate, and concentrated under vacuum to result pure diphenylmethylpiperazine compounds (2a–c) as a white to off-white solid with yields up to 88percent.

Uses

Cinnarizine (C465300) impurity.

Computed Properties

Molecular Weight:252.35
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:252.162648646
Monoisotopic Mass:252.162648646
Topological Polar Surface Area:15.3
Heavy Atom Count:19
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzaldehyde

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