Sodium borohydride → 1-[2-(4-Chlorophenyl)ethyl]-6-methyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 893322Notes

Reaction equation

HRID 893322 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[N:9][CH2:8][CH2:7]2>C(O)C>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][CH:10]2[C:11]3[C:6](=[CH:5][C:4]([CH3:3])=[C:13]([O:14][CH3:15])[CH:12]=3)[CH2:7][CH2:8][NH:9]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 197396936-Methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline

Product 1

HCID 198922341-[2-(4-Chlorophenyl)ethyl]-6-methyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium borohydride (2.0 g) to a suspension of the dihydroisoquinoline from step B (4.75 g) in ethanol (175 mL) and stir the mixture for 2 h. Concentrate to a residue, treat with water and heat on a steam bath for 0.75 h. Cool the mixture to room temperature, extract with ether and concentrate the ethereal extract to a residue. Dissolve the residue in ethyl acetate, treat with 1.7 g of maleic acid and recrystallize the resulting salt from ethanol/ethyl acetate to give the title compound as the maleate salt (4.05 g). Elemental analysis: calc. for C19H22ClNO2, C=63.9%, H=6.03%, N=3.25%; found, C=63.91, H=5.99, N=3.22.

Workup

  1. concentrationConcentrate to a residue
  2. additiontreat with water
  3. temperatureheat on a steam bath for 0.75 h
  4. extractionextract with ether
  5. concentrationconcentrate the
  6. extractionethereal extract to a residue
  7. dissolutionDissolve the residue in ethyl acetate
  8. additiontreat with 1.7 g of maleic acid
  9. customrecrystallize the resulting salt from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-37bac0cd88164200a6d5f718191aff38
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

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