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

HRID 978558Notes

Reaction equation

HRID 978558 reaction equation
O=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([CH2:14][NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:8]1([CH2:7][N:6]2[CH2:2][CH2:3][CH:4]([CH2:14][NH:15][CH2:16][C:17]([F:20])([F:18])[F:19])[CH2:5]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21289038HCID 21289038, compound

Product 1

HCID 14280884[(1-Benzylpyrrolidin-3-yl)methyl](2,2,2-trifluoroethyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8.50 g (28.3 mole) of 5-oxo-1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinemethanamine in 100 ml tetrahydrofuran was added dropwise to 3.22 g (84.9 mmole) of lithium aluminum hydride in 50 ml tetrahydrofuran. The reaction was refluxed two hours, then stirred at room temperature overnight. The reaction was cooled in an ice bath and 3.2 ml of water, 3.2 ml of 15% sodium hydroxide, and 9.6 ml of water were added. The precipitated salts were filtered and washed with hot ethanol. The combined filtrates were concentrated under reduced pressure. The residue was taken up in dichloromethane, filtered, and dried over magnesium sulfate. The solvent was removed at reduced pressure to give 7.15 g of 1-(phenylmethyl-N-(2,2,2-trifluoroethyl)-3-pyrrolidinemethanamine.

Workup

  1. temperatureThe reaction was refluxed two hours
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationThe precipitated salts were filtered
  4. washwashed with hot ethanol
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. filtrationfiltered
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-63b4bb3374b04db8a030355bc34302c4
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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