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

HRID 1089814Notes

Reaction equation

HRID 1089814 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 3 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 1 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-dimethoxybenzyl alcohol hydrochloride (m.p. 223°-226° C.).

Workup

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

Sources & evidence

ORD record
ord-c1f9d181d4df4f5dabbb60d8e759fe36
Source dataset
uspto-grants-1992_01
Patent number
US05079256

Reaction notes

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