Toluene → 4-(2-Naphthoyl-1-piperidyl)-1-phenyl-1-butanone hydrochloride

HRID 1389872Notes

Reaction equation

HRID 1389872 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=CC=CC=3)[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[Cl:20][CH2:21][CH2:22][C:23](=O)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[K+].[C:34](=[O:37])(O)[O-].[K+].[C:39]1(C)[CH:44]=CC=C[CH:40]=1>>[ClH:20].[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][C:23]=1[C:34]([CH:40]1[CH2:39][CH2:44][CH2:6][CH2:7][N:2]1[CH2:3][CH2:4][CH2:5][C:8]([C:10]1[CH:11]=[CH:12][CH:17]=[CH:18][CH:19]=1)=[O:9])=[O:37]

Participants

6

Reactant 5

HCID 1140TolueneHCID 4875Potassium IodideHCID 516893Potassium BicarbonateHCID 134448694-Chloro-1-phenylbutanoneHCID 202955472-Naphthyl 4-piperidyl ketone hydrochloride

Product 1

HCID 202956384-(2-Naphthoyl-1-piperidyl)-1-phenyl-1-butanone hydrochloride

Procedure

A solution of 16 g (37 mmoles) of 2-naphthyl 4-piperidyl ketone hydrochloride 13 g (71 mmoles) of 4-chloro-1-phenylbutanone, 0.1 g of potassium iodide and 30 g potassium bicarbonate in 100 ml of toluene is heated for 48 hours with stirring on a steam bath. The mixture is partitioned between 100 ml portions of toluene and water and the organic phase dried over MgSO4. A solution of an excess HCl in ether is added and the resulting precipitate recrystallized from methanol/butanone to yield 4-(2-naphthoyl-1-piperidyl)-1-phenyl-1-butanone hydrochloride. M.P. 197°-9°.

Workup

  1. customThe mixture is partitioned between 100 ml portions of toluene and water
  2. dry with materialthe organic phase dried over MgSO4
  3. additionA solution of an excess HCl in ether is added
  4. customthe resulting precipitate recrystallized from methanol/butanone

Sources & evidence

ORD record
ord-496b1294e52d4f8685fd54acf0ed3f7a
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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