Phosphorus oxychloride → 2-Methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-6,7-dihydro-thieno[3,2-c]pyridine

HRID 563923Notes

Reaction equation

HRID 563923 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][NH:9][C:10](=O)[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>C(#N)C>[CH3:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][N:9]=[C:10]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59819988N-[2-(5-Methyl-thiophen-2-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide

Product 1

HCID 598200122-Methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-6,7-dihydro-thieno[3,2-c]pyridineYield 102.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 762 mg (2.23 mmol) N-[2-(5-methyl-thiophen-2-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide in 10 mL acetonitrile was added 460 uL (4.91 mmol) POCl3. The mixture was heated to reflux for 1 h and the solvent was removed in vacuo. The residue was taken up in toluene and concentrated again in vacuo. The oil was dissolved in dichloromethane and was basified with sat. NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. 740 mg of the title compound was isolated which was used without further purification in the consecutive step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customthe solvent was removed in vacuo
  4. concentrationconcentrated again in vacuo
  5. dissolutionThe oil was dissolved in dichloromethane
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3c4184e1b6b46f1b99bdb6b443e5ffe
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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