[(1-Benzylpyrrolidin-3-yl)methyl](2,2,2-trifluoroethyl)amine → (Pyrrolidin-3-ylmethyl)(2,2,2-trifluoroethyl)amine

HRID 464987Notes

Reaction equation

HRID 464987 reaction equation
C1(C[N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH2:9]2)C=CC=CC=1.[H][H]>[Pd].CO>[F:19][C:16]([F:17])([F:18])[CH2:15][NH:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 14280884[(1-Benzylpyrrolidin-3-yl)methyl](2,2,2-trifluoroethyl)amineHCID 178418361HCID 178418361, compound

Product 1

HCID 13491797(Pyrrolidin-3-ylmethyl)(2,2,2-trifluoroethyl)amineYield 53.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7.15 g (26.3 mmole) 1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinemethanamine 100 ml of methanol and 0.7 g of 20% palladium on carbon was shaken in an atmosphere of hydrogen at about 4.5×105Pa and at room temperature for 24 hours. The catalyst was filtered and the filtrate evaporated under reduced pressure. The residue was distilled under vacuum (63°-65° C., 2.8 mm Hg) to give 2.55 g of N-(2,2,2-trifluoroethyl)-3-pyrrolidinemethanamine.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. distillationThe residue was distilled under vacuum (63°-65° C., 2.8 mm Hg)

Sources & evidence

ORD record
ord-86d5fd1272ea41a2a885b95d454fdbe6
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

Loading…