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

HRID 464960Notes

Reaction equation

HRID 464960 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 50 psi and at room temperature for 24 hours. The catalyst was filtered and the filtrate evaporated under reduced pressure. The residue was distilled under vacuum, bp 63°-65° C. (2.8 mm), 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, bp 63°-65° C. (2.8 mm)

Sources & evidence

ORD record
ord-afe0714868cf41b0aac0057d9dd50954
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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