6-Acetyl-3-(2-chloroethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine → 6-Acetyl-3-(2-dimethylaminoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

HRID 2294827Notes

Reaction equation

HRID 2294827 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15]Cl)=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[CH3:17][NH:18][CH3:19].C(O)C>>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15][N:18]([CH3:19])[CH3:17])=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 214718566-Acetyl-3-(2-chloroethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridineHCID 22184060Dimethylamine ethanol

Product 1

HCID 214720036-Acetyl-3-(2-dimethylaminoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine

Conditions

Temperature
80 °C

Procedure

A mixture of 0.8 g of 6-acetyl-3-(2-chloroethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine and 20 ml of 16.8% dimethylamine-ethanol solution in a pressure bottle was stirred at 80° C. for 5 hours and then the solvent was distilled away. To the residue was added water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated in vacuo to give 0.4 g of 6-acetyl-3-(2-dimethylaminoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine as an oil.

Workup

  1. distillationthe solvent was distilled away
  2. additionTo the residue was added water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-368ae136870f46cfa67d589dde25af67
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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