Hydrochloric Acid → (4-Methoxyphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride

HRID 1493192Notes

Reaction equation

HRID 1493192 reaction equation
[ClH:1].[CH2:2]=[O:3].CO[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1(C=O)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29]([O-])([O-])=O.[K+].[K+].Cl.[OH2:36]>CN(C=O)C.CCOCC.CO.CCOC(C)=O>[ClH:1].[CH3:2][O:3][C:11]1[CH:10]=[CH:9][C:8]([C:7]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:16][CH2:17]2)=[O:36])=[CH:29][CH:6]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 198068894-(Methoxyphenyl)(4-piperidinyl)methanoneHCID 19933572Methanone hydrochloride

Product 1

HCID 14257843(4-Methoxyphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

(4-Methoxyphenyl)1-(2-phenylethyl)-4-piperidinyl]-methanone HCl. A reaction mixture containing 4-(methoxyphenyl)(4-piperidinyl)methanone (10.3 g, 0.047 mol), 2-bromoethylbenzene (9.57 g, 0.052 mol, 7.1 ml) and K2CO3 (15.2 g, 0.11 mol) in dry DMF (100 ml) was stirred at 90° for 65 h. The cooled reaction mixture was poured into H2O (500 ml) and extracted with toluene (3×100 ml). The extracts were washed with H2O, saturated aqueous NaCl solution and dried over MgSO4. The mixture was filtered and the filtrate concentrated to a residue which was triturated with hexane and filtered. The resulting precipitate (0.022 mol) was dissolved in dry Et2O and treated with a solution of HCl (0.022 mol) in CH3OH/EtOAc (2:5, 14 ml) to give a precipitate which was twice recrystallized from EtOH/Et2O, to give (4-methoxyphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride, mp 238.5°-239.5° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with toluene (3×100 ml)
  3. washThe extracts were washed with H2O, saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated to a residue which
  7. customwas triturated with hexane
  8. filtrationfiltered
  9. customto give a precipitate which
  10. customwas twice recrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-157e2a6ce1bd440fa670753af77776eb
Source dataset
uspto-grants-1991_06
Patent number
US05021428

Reaction notes

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