Water → N-(alpha-methylcinnamoyl)-N-(1-benzyl-4-piperidinyl)aniline

HRID 483490

Reaction equation

HRID 483490 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][C:29](=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:30](Cl)=[O:31].O>C(OC(C)C)(C)C>[CH3:28][C:29](=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:30]([N:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70865N-Phenyl-1-(phenylmethyl)-4-piperidinamineHCID 230201alpha-Methylcinnamoylchloride

Product 1

HCID 54264746N-(alpha-methylcinnamoyl)-N-(1-benzyl-4-piperidinyl)anilineYield 90.2%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

Procedure

To a mixture of N-(1-benzyl-4-piperidinyl)aniline (6.4 g), diisopropyl ether (70 ml) and triethylamine (4.8 ml) is added at 70° C. a solution of α-methylcinnamoyl chloride (4.9 g) in diisopropyl ether (10 ml). After stirring at the same temperature for 30 minutes, water is added to the reaction solution and the mixture is extracted with ethyl acetate. The extract is concentrated by distilling off the solvent and to the resulting residue is added diethyl ether and the formed crystals are separated by filtration to give N-(α-methylcinnamoyl)-N-(1-benzyl-4-piperidinyl)aniline (8.9 g), m.p. 150°-152° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. concentrationThe extract is concentrated
  3. distillationby distilling off the solvent
  4. additionto the resulting residue is added diethyl ether
  5. customthe formed crystals are separated by filtration

Sources & evidence

ORD record
ord-4d9f6a71c1634e9e84c3e79c2f9ee452
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Linked notes

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