Hydrochloric Acid → 1-Benzoyl-3-[3-(4-benzyl-4-cyanopiperid-1-yl)propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride monohydrate

HRID 377805Notes

Reaction equation

HRID 377805 reaction equation
[CH2:1]([C:8]1([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([N:24]1[CH2:29][CH2:28][CH2:27][C:26]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)([CH2:30][CH2:31][CH2:32]OS(C)(=O)=O)[CH2:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[OH2:23].[ClH:44].[C:16]([N:24]1[CH2:29][CH2:28][CH2:27][C:26]([CH2:30][CH2:31][CH2:32][N:11]2[CH2:10][CH2:9][C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:14]#[N:15])[CH2:13][CH2:12]2)([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)[CH2:25]1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118127101-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(methanesulfonyloxy)propyl]piperidineHCID 185392434-Benzyl-4-cyanopiperidine

Product 1

HCID 227418091-Benzoyl-3-[3-(4-benzyl-4-cyanopiperid-1-yl)propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride monohydrateYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound is prepared by the procedure described in EXAMPLE 4, starting from 2.5 g of 4-benzyl-4-cyanopiperidine, 5 g of the compound obtained in step B of EXAMPLE 1, 3.7 g of K2CO3 and 50 ml of DMF. The product obtained is chromatographed on silica H using DCM and then a DCM/MeOH mixture (97/3; v/v) as the eluent. The product obtained is taken up with ethereal hydrogen chloride and the solvent is evaporated off under vacuum to give 2.8 g of the expected product after crystallization from iso ether.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe product obtained
  3. customis chromatographed on silica H
  4. customThe product obtained
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-48f47b187aee4031a2f706de03171b38
Source dataset
uspto-grants-2000_02
Patent number
US06028082

Reaction notes

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