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

HRID 1872685Notes

Reaction equation

HRID 1872685 reaction equation
[I-].[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N+:7]([CH3:13])=[CH:8]2.[BH4-].[Na+]>CO.O>[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH3:13])[CH2:8]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

Procedure

To an ice cold solution of 5-amino-2-methylisoquinolinium iodide (18.8 g, 65 mmol) in methanol (1.5L) and water (60 ml) was added sodium borohydride (17.8 g, 0.47 mol) portionwise over 2h. The mixture was then allowed to stir at room temperature for 18h before concentration in vacuo and partitioning of the residue between water and dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the title compound (8.87 g).

Workup

  1. custompartitioning of the residue between water and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77aab976e3ee4f28a112e2b2893612ca
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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