Methanesulfonic Acid → 4-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone methanesulfonate

HRID 1389877Notes

Reaction equation

HRID 1389877 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:24])[CH2:16][CH2:15]1)=[O:13])[CH:6]=[CH:5]2.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>C(#N)C>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:24])[CH2:16][CH2:15]1)=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 202956124-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

Product 1

HCID 867374524-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone methanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 4-[4-(6-chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone prepared in Example 25 is dissolved in acetonitrile and 0.6 ml (9.2 mmoles) of methanesulfonic acid added. The mixture is stirred for 5 minutes and concentrated in vacuo and the residue stirred in anhydrous ether for 18 hours. The ether is decanted and the residue recrystallized from butanone and toluene to yield 4-[4-(6-chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone methanesulfonate. M.P. 172°-5°.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringthe residue stirred in anhydrous ether for 18 hours
  3. customThe ether is decanted
  4. customthe residue recrystallized from butanone and toluene

Sources & evidence

ORD record
ord-463e7ee597334b7f9e6549fc352cdc8f
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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