Hydrochloric Acid → alpha-(Aminomethyl)-6-fluoro-3,4-dimethoxybenzyl alcohol hydrochloride

HRID 2352267Notes

Reaction equation

HRID 2352267 reaction equation
[C:1]([CH:3]([OH:15])[C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1)#[N:2].B.CO.[ClH:19]>O1CCCC1>[ClH:19].[NH2:2][CH2:1][CH:3]([OH:15])[C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 38339432-(2-Fluoro-4,5-dimethoxyphenyl)-2-hydroxyacetonitrile

Product 1

HCID 14719567alpha-(Aminomethyl)-6-fluoro-3,4-dimethoxybenzyl alcohol hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3.24 g α-(cyano)-6-fluoro-3,4-dimethoxybenzyl alcohol obtained in Reference Example 1 in 20 ml tetrahydrofuran, was added dropwise 33 ml of 1M solution of borane in tetrahydrofuran with stirring in a methanol/ice bath under an argon gas atmosphere, and the resulting solution was heated under reflux for three hours. After cooling the reaction mixture in an ice bath, methanol was added until gas evolution was no longer observed, the resulting solution was stirred at room temperature for one hour, and hydrogen chloride gas was introduced until the pH fell below 1. The crystals which separated out were collected, affording 3.34 g of α-(aminomethyl)-6-fluoro-3,4-dimethoxybenyl alcohol hydrochloride, m.p. 223°-226° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for three hours
  3. temperatureAfter cooling the reaction mixture in an ice bath
  4. stirringthe resulting solution was stirred at room temperature for one hour
  5. customThe crystals which separated out
  6. customwere collected

Sources & evidence

ORD record
ord-28ad3c819b3c43a1b5fb0d1ce9947d85
Source dataset
uspto-grants-1989_10
Patent number
US04876261

Reaction notes

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