(Isocyanatomethylene)dibenzene → N-Benzhydryl-4-(1-(phenyl)-1-(1-methylpiperidin-4-yl)ethyl)piperazine-1-carboxamide

HRID 1992701Notes

Reaction equation

HRID 1992701 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH2:4][CH2:3]1.[C:22]1([CH:28]([N:35]=[C:36]=[O:37])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH:28]([NH:35][C:36]([N:19]1[CH2:18][CH2:17][N:16]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH3:9])[CH2:21][CH2:20]1)=[O:37])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 4250935(Isocyanatomethylene)dibenzeneHCID 597169471-[1-(1-Methylpiperidin-4-yl)-1-phenylethyl]piperazine

Product 1

HCID 11720221N-Benzhydryl-4-(1-(phenyl)-1-(1-methylpiperidin-4-yl)ethyl)piperazine-1-carboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(1-methylpiperidin-4-yl)-1-phenylethyl]piperazine 0.1 g (0.348 mmol) dissolved in methylene chloride (20 ml) was added diphenylmethyl isocyanate 0.073 g (0.348 mmol) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated. The residue was applied to flash column chromatography using methylene chloride and methanol (100:10) as eluents to give 0.15 g of desired product in 87% yield.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d841564b0944955a0e84fd841faf434
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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