Potassium Carbonate → 1-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(N,N-dimethylaminocarbonyl)-4-phenylpiperid-1-yl]propyl]perhydroazepine hydrochloride hemihydrate

HRID 50068

Reaction equation

HRID 50068 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[ClH:18].C(N([C:24]1([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][C:33]2([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=3)[CH2:39][CH2:38][CH2:37][CH2:36][N:35]([C:40](=[O:47])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:34]2)[CH2:26][CH2:25]1)C)(=O)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(#N)C>[OH2:4].[ClH:54].[C:40]([N:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C:33]([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=2)([CH2:32][CH2:31][CH2:30][N:8]2[CH2:7][CH2:6][C:5]([C:3]([N:2]([CH3:17])[CH3:1])=[O:4])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)[CH2:34]1)(=[O:47])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1.[C:40]([N:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C:33]([CH2:32][CH2:31][CH2:30][N:27]2[CH2:28][CH2:29][C:24]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:3]([N:2]([CH3:17])[CH3:1])=[O:4])[CH2:25][CH2:26]2)([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=2)[CH2:34]1)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[ClH:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 417393N,N-dimethyl-4-phenylpiperidine-4-carboxamideHCID 227417463-[3-[4-(Acetyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)perhydroazepine hydrochloride

Product 1

HCID 1317216561-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(N,N-dimethylaminocarbonyl)-4-phenylpiperid-1-yl]propyl]perhydroazepine hydrochloride hemihydrateYield 80.2%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

This compound is prepared by the procedure described in step D of EXAMPLE 13, starting from 0.69 g of 4-(N,N-dimethylaminocarbonyl)-4-phenyl-piperidine, 1.2 g of the compound obtained in step C of EXAMPLE 13 and 1.2 g of K2CO3 in 20 ml of a DMF/acetonitrile mixture (50/50; v/v). This gives 0.65 g of the expected product, m.p.=150° C.

Workup

  1. customThis compound is prepared by the procedure

Sources & evidence

ORD record
ord-0142b026401141c2b99136f61598949b
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Linked notes

Loading…