Hydrochloric Acid → 3-[3-[4-(Aminomethyl)-4-benzylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine dihydrochloride hemihydrate

HRID 377806Notes

Reaction equation

HRID 377806 reaction equation
O.[ClH:2].[C:3]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([CH2:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][C:31]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:34]#[N:35])[CH2:30][CH2:29]2)([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CCO.[Ni]>[OH2:10].[ClH:23].[ClH:2].[NH2:35][CH2:34][C:31]1([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][C:13]2([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:14][CH2:15][CH2:16][N:11]([C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:12]2)[CH2:29][CH2:30]1.[NH2:35][CH2:34][C:31]1([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][C:13]2([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:14][CH2:15][CH2:16][N:11]([C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:12]2)[CH2:29][CH2:30]1.[ClH:23].[ClH:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 227418091-Benzoyl-3-[3-(4-benzyl-4-cyanopiperid-1-yl)propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride monohydrate

Product 1

HCID 1317216533-[3-[4-(Aminomethyl)-4-benzylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine dihydrochloride hemihydrateYield 111.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.3 g of the compound obtained in EXAMPLE 8 and 0.3 g of Raney® nickel in 100 ml of EtOH is hydrogenated for 72 hours at RT and at atmospheric pressure. The catalyst is filtered off and the filtrate is concentrated under vacuum. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (8515; v/v) as the eluent. The product obtained is taken up with ethereal hydrogen chloride and the precipitate formed is filtered off to give 1.08 g of the expected product.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe residue is chromatographed on silica H
  4. customThe product obtained
  5. customthe precipitate formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-21b07574511a4d60986ff9426c70f8bc
Source dataset
uspto-grants-2000_02
Patent number
US06028082

Reaction notes

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