Acrylonitrile → HCID 67915943, compound

HRID 1165032Notes

Reaction equation

HRID 1165032 reaction equation
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.[C:22](#[N:25])[CH:23]=[CH2:24]>CC(O)C>[OH2:7].[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:24][CH2:23][C:22]#[N:25])[CH2:11][C@H:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 7855Acrylonitrile2×HCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamide

Product 1

HCID 67915943HCID 67915943, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred and refluxed solution of 103 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide in 640 parts of 2-propanol were added 19.7 parts of 2-propenenitrile. The mixture was stirred overnight at reflux temperature and then over weekend at room temperature. Another portion of 3 parts of propenenitrile was added to the mixture at reflux. After stirring for 3 hours at reflux temperature, the reaction mixture was evaporated, yielding 121 parts (100%) of cis-4-amino-5-chloro-N-[1-(2-cyanoethyl)-3-methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate (interm. 1).

Workup

  1. stirringThe mixture was stirred overnight
  2. temperatureat reflux temperature
  3. waitover weekend at room temperature
  4. temperatureat reflux
  5. stirringAfter stirring for 3 hours
  6. temperatureat reflux temperature
  7. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-f793eeb950a747c6bd67627c610543dc
Source dataset
uspto-grants-1990_03
Patent number
US04906643

Reaction notes

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