Sodium borohydride → (4-(Aminomethyl)-3-methylphenyl)(2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methanone

HRID 558945Notes

Reaction equation

HRID 558945 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[CH:20][CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+]>CO.[Co](Cl)Cl>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[CH:20][CH:21]=[CH:22][C:13]2=3)=[O:11])=[CH:9][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 158960852-Methyl-4-(2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)benzonitrile

Product 1

HCID 15896086(4-(Aminomethyl)-3-methylphenyl)(2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-4-(2,3,4,5-tetrahydrobenzo[b]azepine-1-carbonyl)benzonitrile from Example F1 (430 mg, 1.48 mmol) in methanol (25 ml) was added cobalt (II) chloride (710 mg, 3.0 mmol) and cooled in an ice/water bath. Sodium borohydride (570 mg, 15 mmol) was added portionwise and the mixture was stirred at room temperature for 1 h. The mixture was evaporated, 1N HCl(aq) (20 ml) was added and stirred for 15 mins. The mixture was filtered through Celite® and the Celite® was washed with 2-propanol:chloroform, 20:80 (100 ml). The mixture was separated and the aqueous layer washed with diethyl ether. The aqueous layer was basified with 2N NaOH(aq), chloroform was added and the mixture filtered through Celite®. The Celite® was washed with chloroform. The mixture was separated and the organic layer dried and evaporated, yield 340 mg, 78%.

Workup

  1. temperaturecooled in an ice/water bath
  2. customThe mixture was evaporated
  3. addition1N HCl(aq) (20 ml) was added
  4. stirringstirred for 15 mins
  5. filtrationThe mixture was filtered through Celite®
  6. washthe Celite® was washed with 2-propanol
  7. customThe mixture was separated
  8. washthe aqueous layer washed with diethyl ether
  9. additionwas added
  10. filtrationthe mixture filtered through Celite®
  11. washThe Celite® was washed with chloroform
  12. customThe mixture was separated
  13. customthe organic layer dried
  14. customevaporated

Sources & evidence

ORD record
ord-1dce723ec1454d1680b1738d31b40fea
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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