PyBroP → 1-Cyclopropylmethyl-piperidine-4-carboxylic Acid 4-[(4-chloro-phenyl)-methyl-carbamoyl]-2-methyl-benzylamide

HRID 220976Notes

Reaction equation

HRID 220976 reaction equation
C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:25]1([CH2:28][N:29]2[CH2:34][CH2:33][CH:32]([C:35]([OH:37])=O)[CH2:31][CH2:30]2)[CH2:27][CH2:26]1.[NH2:38][CH2:39][C:40]1[CH:56]=[CH:55][C:43]([C:44]([N:46]([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)[CH3:47])=[O:45])=[CH:42][C:41]=1[CH3:57]>ClCCl.CN(C=O)C>[Cl:54][C:51]1[CH:52]=[CH:53][C:48]([N:46]([CH3:47])[C:44]([C:43]2[CH:55]=[CH:56][C:40]([CH2:39][NH:38][C:35]([CH:32]3[CH2:31][CH2:30][N:29]([CH2:28][CH:25]4[CH2:26][CH2:27]4)[CH2:34][CH2:33]3)=[O:37])=[C:41]([CH3:57])[CH:42]=2)=[O:45])=[CH:49][CH:50]=1

Participants

6

Reactant 3

HCID 2733179PyBroPHCID 162440151-(Cyclopropylmethyl)piperidine-4-carboxylic acidHCID 575552204-Aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide

Product 1

HCID 575552361-Cyclopropylmethyl-piperidine-4-carboxylic Acid 4-[(4-chloro-phenyl)-methyl-carbamoyl]-2-methyl-benzylamideYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

PyBroP (212 mg, 0.45 mmol) and 1-cyclopropylmethyl-piperidine-4-carboxylic acid from Example E15a (76 mg, 0.42 mmol) were added to a solution of 4-aminomethyl-N-(4-chloro-phenyl)-3,N-dimethyl-benzamide from Example E115.2 (100 mg, 0.35 mmol) in dichloromethane (5 ml) and DMF (1 ml). The mixture was stirred at room temperature for 18 h then solvents were removed in vacuo and azeotroped with toluene. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white powder identified as the title compound (34 mg, 22%).

Workup

  1. customsolvents were removed in vacuo
  2. customazeotroped with toluene
  3. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  4. customto give a white powder

Sources & evidence

ORD record
ord-5fa44f0e8aa5453aafc98b718fae9abc
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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