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

HRID 50062Notes

Reaction equation

HRID 50062 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].Cl.[C:30]([N:38]1[CH2:43][CH2:42][CH2:41][C:40]([C:60]2[CH:65]=[CH:64][C:63]([Cl:66])=[C:62]([Cl:67])[CH:61]=2)([CH2:44][CH2:45][CH2:46]N2CCC(C(N3CCCC3)=O)CC2)[CH2:39]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.O>[OH2:8].[OH2:14].[ClH:66].[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]([CH2:46][CH2:45][CH2:44][C:40]2([C:60]3[CH:65]=[CH:64][C:63]([Cl:66])=[C:62]([Cl:67])[CH:61]=3)[CH2:41][CH2:42][CH2:43][N:38]([C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:39]2)[CH2:20][CH2:21]1)(=[O:14])[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 227417141-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine hydrochlorideHCID 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 132.7%

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-toluene-sulfonate, 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 93/7; 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-c5b82c17f3e74bf885a0bb91dab2f7ca
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Reaction notes

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