Hydrochloric Acid → 3-[4-(Trifluoromethyl)phenyl]pyrrolidine

HRID 552680Notes

Reaction equation

HRID 552680 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][NH:11][CH2:12][CH:13]=2)=[CH:5][CH:4]=1.Cl>CO.CCOCC>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 590304773-(4-Trifluoromethyl-phenyl)-2,5-dihydro-1H-pyrrole

Product 1

HCID 38657063-[4-(Trifluoromethyl)phenyl]pyrrolidineYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.08 mmol 3-(4-Trifluoromethyl-phenyl)-2,5-dihydro-1H-pyrrole was dissolved in MeOH and HCl in ether was added until pH 1. After 5 minutes stirring, the solvents were evaporated. To a solution of this salt in 0.7 ml methanol under argon was added 2 mg Pd/C 10% and the mixture was hydrogenated under atmospheric pressure of hydrogen at room temperature for 4 h. The mixture was cooled, flushed with argon, diluted with methanol, filtered and the solvent was removed in vacuo to yield the title compound (64%) as an oil MS (m/e): 216.3 ([M+1], 100%).

Workup

  1. customthe solvents were evaporated
  2. additionTo a solution of this salt in 0.7 ml methanol under argon was added 2 mg Pd/C 10%
  3. waitthe mixture was hydrogenated under atmospheric pressure of hydrogen at room temperature for 4 h
  4. temperatureThe mixture was cooled
  5. customflushed with argon
  6. additiondiluted with methanol
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f915434dc0a84b21b8d9a0692eda7c09
Source dataset
uspto-grants-2011_05
Patent number
US07951836B2

Reaction notes

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