Sodium borohydride → 2-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

HRID 650520Notes

Reaction equation

HRID 650520 reaction equation
[BH4-].[Na+].[I-].[NH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([CH3:15])=[CH:10]2>CO.O>[NH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9]([CH3:15])[CH2:10]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11426171HCID 11426171, compound

Product 1

HCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amineYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Sodium borohydride (17.8 g, 0.47 mol) was added portionwise over 2 h to an ice cold solution of 5-amino-2-methylisoquinolinium iodide (18.8 g, 65 mmol) in methanol (1.5 L) and water (60 ml). The mixture was then stirred at 25° C. for 18 h. and concentrated in vacuo. The residue was extracted into water and dichloromethane. The organic layer was dried (Na2SO4) and concentration in vacuo gave the title compound (8.87 g).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted into water and dichloromethane
  3. customThe organic layer was dried
  4. concentration(Na2SO4) and concentration in vacuo

Sources & evidence

ORD record
ord-b621f215c36b4f7a833c1e11eea00507
Source dataset
uspto-grants-2001_08
Patent number
US06274594B1

Reaction notes

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