N-Methylbenzylamine → HCID 86751299, compound

HRID 1379199Notes

Reaction equation

HRID 1379199 reaction equation
Cl.[F:2][C:3]([F:36])([F:35])[C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][C@H:10]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:8].[CH3:37][NH:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C.[I-].[Cl:54]C1C=CC=C[N+]=1C>ClCCl>[ClH:54].[F:35][C:3]([F:36])([F:2])[C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:30]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16](=[O:18])[N:38]([CH3:37])[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:11][C@H:10]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=1)=[O:8]

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 86751301HCID 86751301, compound

Product 1

HCID 86751299HCID 86751299, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(carboxymethyl)piperazine hydrochloride (210 mg), N-methylbenzylamine (52 mg) and triethylamine (0.19 ml) in dichloromethane (5 ml) was added 2-chloro-1-methylpyridinium iodide (110 mg) under nitrogen atmosphere at room temperature. The mixture was stirred at the same temperature for 1 hour. After removal of the solvent, the residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (10:1). The eluate was concentrated and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[(N-methyl-N-benzylcarbamoyl)methyl]piperazine hydrochloride (190 mg) as a powder.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (10:1)
  3. concentrationThe eluate was concentrated
  4. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-25e26f1f836942de81d52c6c22341467
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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