Hydrochloric Acid → HCID 14257839, compound

HRID 1165858Notes

Reaction equation

HRID 1165858 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+].Br[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[ClH:32]>C1(C)C=CC=CC=1.CCOC(C)=O>[ClH:32].[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:11][CH2:10]2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 226102Phenyl(piperidin-4-yl)methanone

Product 1

HCID 14257839HCID 14257839, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture containing phenyl(4-piperidinyl)methanone (20.5 g, 0.108 mol), K2CO3 (33.17 g, 0.18 mol), potassium iodide (0.2 g) and 2-bromoethyl benzene (22.2 g, 0.12 mol, 16.4 ml) in toluene (250 ml) was stirred at reflux temperature for 66 h. The reaction mixture was filtered and the filtrate concentrated to a residue which was dissolved in dry Et2O (500 ml) and treated dropwise with a solution of HCl (0.11 mol) in EtOAc. The resultant precipitate was recrystallized from EtOH:CH3OH, 4:1 (500 ml) to give phenyl[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride, mp 258°-260° C.

Workup

  1. temperatureat reflux temperature for 66 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated to a residue which
  4. dissolutionwas dissolved in dry Et2O (500 ml)
  5. customThe resultant precipitate was recrystallized from EtOH

Sources & evidence

ORD record
ord-1cf373d5dd53452883802b32aff1098e
Source dataset
uspto-grants-1990_03
Patent number
US04912117

Reaction notes

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