Potassium Iodide → 1-(2-Phenylethyl)piperidinyl-methanone hydrochloride

HRID 1493194Notes

Reaction equation

HRID 1493194 reaction equation
[ClH:1].C=O.CC(C1C=CC(C([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=O)=CC=1)C.Br[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]([O-])([O-])=[O:31].[K+].[K+].[I-].[K+]>C1(C)C=CC=CC=1>[ClH:1].[C:24]1([CH2:23][CH2:22][N:18]2[CH2:17][CH2:16][CH2:15][CH2:20][CH:19]2[CH:30]=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 19933572Methanone hydrochlorideHCID 222382884-[4-(Propan-2-yl)benzoyl]piperidine

Product 1

HCID 867448161-(2-Phenylethyl)piperidinyl-methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

[4-(1-methylethyl)phenyl]1-(2-phenylethyl)-piperidinyl]-methanone HCl. A solution of [4-(1-methylethyl)phenyl](4-piperidinyl)-methanone (43 g, 0.19 mol) in toluene (500 ml) was treated with 2-bromoethylbenzene (37 g, 0.2 mol), K2CO3 (25 g, 0.18 mol), KHCO3 (25 g, 0.25 mol) and potassium iodide (0.1 g) and the mixture heated on a steam bath for 68 h. The reaction mixture was filtered and the filtrate treated with ethereal hydrogen chloride until acid to congo red indicator paper. The resultant precipitate was filtered off and recrystallized twice from CH3OH/butanone to give [4-(1-methylethyl)-phenyl][1-(2-phenylethyl)piperidinyl-methanone hydrochloride, mp 251°-253° C. By following the sodium borohydride reduction procedure of the foregoing example there is obtained the desired product of this example.

Workup

  1. temperaturethe mixture heated on a steam bath for 68 h
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate treated with ethereal hydrogen chloride until acid to congo red indicator paper
  4. filtrationThe resultant precipitate was filtered off
  5. customrecrystallized twice from CH3OH/butanone

Sources & evidence

ORD record
ord-9c04e6c0bfa94dab84e911d742e1aa08
Source dataset
uspto-grants-1991_06
Patent number
US05021428

Reaction notes

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