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Home > Encyclopedia > 4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid

4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid

4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid structure

4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid 

structure
  • CAS No:

    85098-64-2

  • Formula:

    C19H22N2O2

  • Chemical Name:

    4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid

  • Synonyms:

    4-Piperidinecarboxylic acid,4-(phenylamino)-1-(phenylmethyl)-;4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid;NSC 73748;1-Benzyl-4-(phenylamino)piperidine-4-carboxylic acid;4-Anilino-1-benzylpiperidine-4-carboxylic acid

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Grey Solid

4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid Basic Attributes

310.39018

310.39

285-415-7

B4386XQ54S

73748

DTXSID60234187

2933399090

Characteristics

52.6

1.1

Pale yellow powder

1.2±0.1 g/cm3

243-245 °C

495.6°C at 760 mmHg

253.5±28.7 °C

1.644

4-(Phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylic acid Use and Manufacturing

Methods of Manufacturing

1-Benzyl-4-(phenylamino)piperidine-4-carboxylic acid To a solution of aniline (2 g, 21 mmol) in tetrahydrofuran was added sodium hydroxide (4.3 g, 107 mmol) at 0°C. After stirring for 10 minutes at 0°C, to the resulting solution was added ferf-butyl 4-oxopiperidine-1 - carboxylate (43 g, 21 .6 mmol). The resulting suspension was stirred for 20 minutes at 0°C. To the suspension was added chloroform (12.7 g, 107 mmol). The reaction was stirred overnight before quenching with water (10 mL). The resulting mixture was extracted with ethyl acetate (100 mL). The pH of aqueous layer was adjusted to pH 3 by addition of 5percent aqueous hydrochloride solution and extracted with ethyl acetate (3 χ 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to afford 1 -benzyl-4-(phenylamino)piperidine-4- carboxylic acid as a brown solid (0.38 g, 8percent). LCMS (ESI): m/z = 311 .2 [M+H]

Uses

A piperidine derivative as potential analgesic agent

Computed Properties

Molecular Weight:310.4
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:310.168127949
Monoisotopic Mass:310.168127949
Topological Polar Surface Area:52.6
Heavy Atom Count:23
Complexity:379
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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