Acetic Acid → HCID 20366154, compound

HRID 616844Notes

Reaction equation

HRID 616844 reaction equation
[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)#[N:2].C(O)(=[O:35])C.ClC1C=CC=C(C(OO)=O)C=1>O>[C:1]([C:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:4][CH2:5][N+:6]1([O-:35])[CH2:11][CH2:10][C:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 34328DifenoxinHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 20366154HCID 20366154, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.3 Grams of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid was dissolved, at room temperature, in 100 ml. of glacial acetic acid. To that mixture was added 3.1 grams of m-chloroperbenzoic acid (85% by weight) and the resultant mixture was stirred at room temperature for a period of 11/2 hours, thereafter diluted with 500 ml. of water, cooled and filtered. The residual solid was washed successively with water chloroform, ether and warm methanol. Upon drying for 6 hours at 65° C. was afforded 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-N-oxidopiperidine-4-carboxylic acid, melting at about 186°-189° C., with decomposition.

Workup

  1. additiondiluted with 500 ml
  2. filtrationfiltered
  3. washThe residual solid was washed successively with water chloroform, ether
  4. temperaturewarm methanol
  5. customUpon drying for 6 hours at 65° C.

Sources & evidence

ORD record
ord-9b01d6ed083b499bb235b4cb060020f6
Source dataset
uspto-grants-1978_02
Patent number
US04076717

Reaction notes

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