Sodium borohydride → 1-(4-Bromophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 397053Notes

Reaction equation

HRID 397053 reaction equation
[BH4-].[Na+].Cl.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]=2)=[CH:7][CH:6]=1>CO>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 181724611-(4-Bromophenyl)-6-methoxy-3,4-dihydroisoquinoline hydrochloride

Product 1

HCID 43161381-(4-Bromophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.720 g, 19.0 mmol) was added in small portions to a solution of 1-(4-bromophenyl)-6-methoxy-3,4-dihydroisoquinoline, hydrochloride (3.62 g, 10.2 mmol) in MeOH (30 ml) at 0° C. The reaction mixture was stirred for 30 min, warmed to rt, and stirred at rt for 1 hr, then quenched by the dropwise addition of H2O (10 ml). Acetic acid (10 drops) was added with stirring, and the resulting mixture was basified to pH 10 with 1N NaOH and extracted with EtOAc (3×25 ml). The combined extracts were washed with 1N NaOH followed by saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo to give 3.24 g (100% yield) of white solid.

Workup

  1. stirringstirred at rt for 1 hr
  2. customquenched by the dropwise addition of H2O (10 ml)
  3. additionAcetic acid (10 drops) was added
  4. stirringwith stirring
  5. extractionextracted with EtOAc (3×25 ml)
  6. washThe combined extracts were washed with 1N NaOH
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87231351aac346acb036eadc66b2b0c2
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…