Ammonia → 4-Aminomethyl-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

HRID 558987Notes

Reaction equation

HRID 558987 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH3:10])=[O:8])=[CH:5][C:4]=1[CH3:24])#[N:2].[BH4-].[Na+].N>CO.O.O.O.O.O.O.[Co+2]>[NH2:2][CH2:1][C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH3:10])=[O:8])=[CH:5][C:4]=1[CH3:24]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 574707864-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

Product 1

HCID 574707874-Aminomethyl-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 5232990Cobalt(2+);hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide from Example 21C (198 mg, 0.626 mmol) in methanol (10 ml) was added cobalt (II) hexahydrate (300 mg, 1.25 mmol). The mixture was cooled in an ice/water bath and sodium borohydride (237 mg, 6.26 mmol) was added portionwise. The mixture was allowed to warm to room temperature and stirred for 2 h. Ammonia solution (4.0 ml) was added and the mixture stirred for 30 min, filtered through Celite® and evaporated in vacuo. The residue was taken up in chloroform and brine, filtered through Celite®, separated and the organic layer was dried and evaporated in vacuo to give a white solid; yield 200 mg, 100%.

Workup

  1. temperatureThe mixture was cooled in an ice/water bath
  2. stirringthe mixture stirred for 30 min
  3. filtrationfiltered through Celite®
  4. customevaporated in vacuo
  5. filtrationbrine, filtered through Celite®
  6. customseparated
  7. customthe organic layer was dried
  8. customevaporated in vacuo
  9. customto give a white solid

Sources & evidence

ORD record
ord-997575af879d441fa8e2437c98b23605
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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