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

HRID 50063Notes

Reaction equation

HRID 50063 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.Cl.[C:17]([N:25]1[CH2:30][CH2:29][CH2:28][C:27]([C:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=2)([CH2:31][CH2:32][CH2:33]N2CCC(C(N3CCCC3)=O)CC2)[CH2:26]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[OH2:24].[ClH:53].[C:17]([N:25]1[CH2:30][CH2:29][CH2:28][C:27]([CH2:31][CH2:32][CH2:33][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:47]2[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=2)[CH2:26]1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 185392434-Benzyl-4-cyanopiperidineHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochloride

Product 1

HCID 227418091-Benzoyl-3-[3-(4-benzyl-4-cyanopiperid-1-yl)propyl]-3-(3,4-dichlorophenyl)piperidine hydrochloride monohydrateYield 105.6%

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-2cbf979eac5642f3b526fa0792c90297
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Reaction notes

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