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

HRID 54683Notes

Reaction equation

HRID 54683 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 106.1%

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-45a7a65e5f184df982197cc7aa2f91bd
Source dataset
uspto-grants-1997_04
Patent number
US05623074

Reaction notes

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