Acetic Acid → STK366646

HRID 1973784Notes

Reaction equation

HRID 1973784 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.[C-:27]#[N:28].[K+]>O>[NH:16]([C:2]1([C:27]#[N:28])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][CH2:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 9032Potassium CyanideHCID 96437N-Phenethyl-4-piperidinone

Product 1

HCID 828001STK366646

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 102 parts of 4-oxo-1-(2-phenyl-ethyl)-piperidine, 47 parts of aniline and 350 parts of acetic acid is added dropwise a solution of 36 parts of potassium cyanide in 100 parts of water, at a temperature between 35°-45° C (exothermic reaction). After the addition is complete, the cooling-bath is removed and the whole is stirred for 20 hours at room temperature. The reaction mixture is poured into 650 parts of ammonium hydroxide and 500 parts of crushed ice are added. The mixture is extracted with chloroform. The organic extract is dried over potassium carbonate, filtered and evaporated. The residue (solid) is triturated in diisopropylether. After keeping at room temperature, 4-anilino-4-cyano-1-(2-phenylethyl)-piperidine is obtained; mp. 120°-121° C.

Workup

  1. customat a temperature between 35°-45° C (exothermic reaction)
  2. additionAfter the addition
  3. customthe cooling-bath is removed
  4. additionThe reaction mixture is poured into 650 parts of ammonium hydroxide and 500 parts of crushed ice
  5. additionare added
  6. extractionThe mixture is extracted with chloroform
  7. extractionThe organic extract
  8. dry with materialis dried over potassium carbonate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue (solid) is triturated in diisopropylether
  12. customAfter keeping at room temperature

Sources & evidence

ORD record
ord-8a836e8de70b488aa7736d0668a65591
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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