Acetic Acid → HCID 12834313, compound

HRID 1065259Notes

Reaction equation

HRID 1065259 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.C(O)(=O)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.[C-:25]#[N:26].[Na+]>O>[C:25]([C:7]1([NH:24][C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH:2]1[CH3:1])#[N:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 97314-FluoroanilineHCID 3015586Methyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 12834313HCID 12834313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 248 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate in 660 parts of acetic acid are added 150 parts of 4-fluorobenzenamine and the whole is stirred for 30 minutes. After cooling with ice-water, a solution of 69 parts of sodium cyanide in 195 parts of water is added dropwise at room temperature. Upon completion, stirring at room temperature is continued over week-end. The solid product is filtered off and washed with 2,2'-oxybispropane and petroleumether, yielding 230 parts of methyl 4-cyano-4-[(4-fluorophenyl)amino]-3-methyl-1-piperidinecarboxylate; mp. 90° C.

Workup

  1. stirringUpon completion, stirring at room temperature
  2. waitis continued over week-end
  3. filtrationThe solid product is filtered off
  4. washwashed with 2,2'-oxybispropane and petroleumether

Sources & evidence

ORD record
ord-d984f8c18cdb4a059492069b7ffb99a6
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

Loading…