Dimethylformamide → HCID 20366149, compound

HRID 616843Notes

Reaction equation

HRID 616843 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].CN(C)C=O.[Cl:38][CH2:39][C:40]#[N:41].C(N(CC)CC)C>O>[ClH:38].[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[CH2:11][CH2:10][C:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:12]([O:14][CH2:39][C:40]#[N:41])=[O:13])[CH2:8][CH2:7]1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 34328Difenoxin

Product 1

HCID 20366149HCID 20366149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.12 Grams of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid was dissolved in 60 ml. of redistilled N,N-dimethylformamide by warming to approximately 60° C. To the resultant solution was added .4 gram of chloracetonitrile, followed by .55 gram of triethylamine. The solution was stirred at room temperature under anhydrous conditions for about 24 hours, then diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, acidified with concentrated hydrochloric acid in 2-propanol, diluted with ethyl ether and cooled. The precipitate which formed was recrystallized from a mixture of methanol and tetrahydrofuran, affording cyanomethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate hydrochloride, melting at about 243.5°-245.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. additiondiluted with ethyl ether
  5. temperaturecooled
  6. customThe precipitate which formed
  7. customwas recrystallized from a mixture of methanol and tetrahydrofuran

Sources & evidence

ORD record
ord-b86e22259b0f4dbabe0336d34dcb1f8b
Source dataset
uspto-grants-1978_02
Patent number
US04076717

Reaction notes

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