Hydrochloric Acid → 3-[3-[4-(Acetylamino)-4-benzylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride dihydrate

HRID 377804Notes

Reaction equation

HRID 377804 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[C:12]([NH:15][C:16]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:14])[CH3:13].[C:29]([N:37]1[CH2:42][CH2:41][CH2:40][C:39]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=2)([CH2:43][CH2:44][CH2:45]OS(C)(=O)=O)[CH2:38]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[OH2:8].[OH2:14].[ClH:57].[C:12]([NH:15][C:16]1([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18][N:19]([CH2:45][CH2:44][CH2:43][C:39]2([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=3)[CH2:40][CH2:41][CH2:42][N:37]([C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:38]2)[CH2:20][CH2:21]1)(=[O:14])[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 118127101-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-(methanesulfonyloxy)propyl]piperidineHCID 227417304-(Acetylamino)-4-benzylpiperidine p-toluene-sulfonate

Product 1

HCID 227417683-[3-[4-(Acetylamino)-4-benzylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride dihydrateYield 105.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.44 g of 4-(acetylamino)-4-benzylpiperidine p-toluenesulfonate, 0.50 g of the compound obtained in step B of EXAMPLE 1 and 0.53 g of K2CO3 in 5 ml of DMF is heated at 90° C. for 2 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with 2 N NaOH and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using a gradient of a DCM/MeOH mixture (99/1; v/v to 9317; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.38 g of the expected product, m.p.=158° C. (dec.).

Workup

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with 2 N NaOH and with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica H
  6. customThe product obtained
  7. customthe precipitate formed
  8. filtrationis filtered off

Sources & evidence

ORD record
ord-a13515f561f04aa88ae1656aeec73fab
Source dataset
uspto-grants-2000_02
Patent number
US06028082

Reaction notes

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