Sodium borohydride → HCID 588676, compound

HRID 361605Notes

Reaction equation

HRID 361605 reaction equation
[C:1]1([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1.[BH4-].[Na+]>CO.O>[CH:1]1([C:11]2[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 539726084-(3,4-Dihydroisoquinolin-1-yl)benzonitrile

Product 1

HCID 588676HCID 588676, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3.48 g of 4-(3,4-dihydro-isoquinolin-1-yl)-benzonitrile in 90 ml of methanol was cooled to 5° C. while stirring and treated with 1.7 g of sodium borohydride within 30 min. After completion of the addition, the mixture was stirred at 5° C. for a further 30 min. Subsequently, 50 ml of water were slowly added dropwise and the mixture was stirred at room temperature for a further 10 min. The mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. 3.15 g of crystalline (RS)-4-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-benzonitrile were obtained. Recrystallization of a sample from diisopropyl ether gave colorless crystals of m.p. 94°-97° C.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at 5° C. for a further 30 min
  3. stirringthe mixture was stirred at room temperature for a further 10 min
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-bc55606960c04fbaa56f3c902fdc940f
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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