Formaldehyde → HCID 13027030, compound

HRID 1759320Notes

Reaction equation

HRID 1759320 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[OH:8].[CH2:23]=O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([CH3:23])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[OH:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 20531713HCID 20531713, compound

Product 1

HCID 13027030HCID 13027030, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 0.96 g (0.003 m) of N-(2-chlorobenzyl)-1-(3,4-dimethoxyphenyl)-2-aminoethanol from Example 5, 3 ml (0.037 m) of formaldehyde and 0.4 g of sodium borohydride in methanol was reacted to give 0.94 g (93%) of N-(2-chlorobenzyl)-1-(3,4-dimethoxyphenyl)-2-methylaminoethanol as an oil. This material (0.6 g., 0.0018 m) and 0.95 g (0.007 m) of aluminum chloride were reacted as described to give 0.42 g (66%) of 8-chloro-4-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, m.p. 212°-217°. This material (0.68 g., 0.002 m) and 1.2 ml (0.013 m) of boron tribromide were reacted to give 0.70 g. (94%) of 8-chloro-4-(3,4-dihydroxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 266°-269°.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-4295e71fa5d44c73a579d3d16b071bb9
Source dataset
uspto-grants-1982_07
Patent number
US04340600

Reaction notes

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