Sodium borohydride → 2-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428794Notes

Reaction equation

HRID 1428794 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>C(O)C>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866802292-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Product 1

HCID 866802302-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (305 mg, 0.72 mmol) in ethanol was cooled to 0° C. and added NiCl2.6H2O (17 mg, 0.072 mmol) and stirred more then 15 min. Sodium borohydride (191 mg, 5.04 mmol) was then added in small portions. The reaction was exothermic and effervescent. The resulting reaction mixture was allowed to warm to room temperature and left to stir for 2 hour. The mixture was filtered using celite pad. The filtrate was concentrated was evaporated. The residue was dissolved in ethylacetate and washed with water and brine, but when it does not separate easily, small amount of 1N HCl and saturated NaHCO3 was used. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg) was obtained as 64% yield.

Workup

  1. custom15 min
  2. customThe resulting reaction mixture
  3. waitleft
  4. stirringto stir for 2 hour
  5. filtrationThe mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. customwas evaporated
  8. dissolutionThe residue was dissolved in ethylacetate
  9. washwashed with water and brine, but when it
  10. customdoes not separate easily
  11. dry with materialThe organic layer was dried over magnesium sulfate
  12. filtrationfiltered
  13. customThe filtrate removed in vacuo
  14. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-25819583d75f4f41a7d205698886a4eb
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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