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Home > Encyclopedia > 4-Hydroxy-1-methylpiperidine

4-Hydroxy-1-methylpiperidine

4-Hydroxy-1-methylpiperidine structure

4-Hydroxy-1-methylpiperidine 

structure
  • CAS No:

    106-52-5

  • Formula:

    C6H13NO

  • Chemical Name:

    4-Hydroxy-1-methylpiperidine

  • Synonyms:

    4-Piperidinol,1-methyl-;1-Methyl-4-piperidinol;1-Methyl-4-hydroxypiperidine;N-Methyl-4-piperidinol;4-Hydroxy-1-methylpiperidine;N-Methyl-4-hydroxypiperidine;4-Hydroxy-N-methylpiperidine;NSC 60705

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

clear colorless to yellowish liquid after melting

4-Hydroxy-1-methylpiperidine Basic Attributes

115.17

115.17

203-406-8

60705

DTXSID9059339

29333999

Characteristics

23.5

0.1

0.98 g/mL at 20 °C(lit.)

29 °C

200 °C

190 °F

n 20/D 1.479

MISCIBLE

Safety Information

NONH for all modes of transport

3

R36/37/38

26-37/39-45-36/37/39-27

Xi,C

P261-P280-P305 + P351 + P338

H315-H318-H335

|Danger|H315 (92.16%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 103 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

4-Hydroxy-1-methylpiperidine Use and Manufacturing

Methods of Manufacturing

In a typical experiment, complex 1 (6.1 mg, 10 tmol) and H[BAr’4].(Et2O)2 (10.1 mg, 10 tmol) were dissolved in THF (2.0 mE) in a 100 mE thick-walled glass vessel equipped with a TEFLON stopcock and a stir bar. The substrate (0.5 mmol) to be hydrogenated was then added. The vessel was degassed by freeze-pump-thaw and then hydrogen (1 or 4 atm) was added. The resulting solution was stirred at the desired temperature (25-60° C.) for the indicated reaction time. At the end of the reaction, the solvent was evaporated and the residue was passed through silica gel in a pipette. The solvent was removed under vacuum and the ‘H NMR spectrum of the crude product mixture was recorded in CDC13. Hydrogenation products were then isolated by column chromatography or preparative thin layer chromatography (“TLC”) using n-hexane/ethyl acetate (3:1, v/v) as an eluent. Isolated products were characterized by ‘H NMR and GCMS, with spectra matching those reported in the literature or authentic samples.A mixture of 4-piperidinol (1.16g, 10.07mmol) and 47percent aqueous formaldehyde solution (10 mL) were dissolved in methanol (10 mL), and acidified with concentrated hydrochloricTo pH 2-3, to the system was added 10percent Pd / C (300mg), two days the reaction system was kept under a hydrogen atmosphere. Completion of the reaction, filtered and the filtrate reducedPressure concentrated and the crude product purified by column chromatography (MeOH) to give a white solid (1.59g, 89percent)

Uses

Reactant for:• ;Optimization of Novobiocin scaffold to product antitumor agents1• ;Substitution about the rigidifying ring for histamine H4 receptor antagonist synthesis2Reactant for synthesis of:• ;CaMKII inhibitors3• ;VEGFR and FGFR kinase inhibitors4• ;Phosphoinositide-3-kinase inhibitors5• ;Protein lysine methyltransferase G9a inhibitors6

4-Piperidinol, 1-methyl-: ACTIVE

Computed Properties

Molecular Weight:115.17
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:115.099714038
Monoisotopic Mass:115.099714038
Topological Polar Surface Area:23.5
Heavy Atom Count:8
Complexity:66.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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