Sodium borohydride → 5-Amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 650944Notes

Reaction equation

HRID 650944 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH3:13])[CH:7]2[CH3:12].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:13])[CH:7]2[CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 217104485-Amino-1,2-dihydro-1,2-dimethyl isoquinoline

Product 1

HCID 217104395-Amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolineYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice cold solution of 5-amino-1,2-dihydro-1,2-dimethyl isoquinoline (4 g, 23.2 mmol) in methanol (80 ml) was added sodium borohydride (3.51 g, 92.8 mmol) portionwise. The mixture was allowed to stir at room temperature overnight before concentration in vacuo; the residue was then partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford a light brown oil (4.023 g).

Workup

  1. customthe residue was then partitioned between water and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4dbccc5d1234b439320822b802a636d
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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