Ammonia → 4-(6-Fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1590840Notes

Reaction equation

HRID 1590840 reaction equation
[C:1]1([CH2:6][NH:7][CH2:8][CH:9](O)[C:10]2[C:15]([F:16])=[CH:14][C:13]([O:17][CH3:18])=[C:12]([O:19][CH3:20])[CH:11]=2)[S:5][CH:4]=[CH:3][CH:2]=1.N>>[F:16][C:15]1[C:10]([CH:9]2[CH2:8][NH:7][CH2:6][C:1]3[S:5][CH:4]=[CH:3][C:2]2=3)=[CH:11][C:12]([O:19][CH3:20])=[C:13]([O:17][CH3:18])[CH:14]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 14719573alpha-[[(2-Thenyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol

Product 1

HCID 199597114-(6-Fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 10,614.1%

Conditions

Temperature
60 °C

Procedure

A mixture of 0.66 g of α-[[(2-thenyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol and 10 ml of polyphosphoric acid was stirred for 3.5 hours at 60° C. The reaction solution was poured into ice water, and the mixture was basified by addition of 25 ml of conc. aqueous ammonia. The mixture was extracted with chloroform, and the chloroform layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and 0./66 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine was obtained as a syrupy matter.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washthe chloroform layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a2ffcdde4bdf4ba5ab2e9550749ceb55
Source dataset
uspto-grants-1993_04
Patent number
US05204468

Reaction notes

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