Lithium aluminum hydride → 2-(4-Chlorophenyl)-2-(pyrrolidin-1-yl)ethan-1-amine

HRID 1482489Notes

Reaction equation

HRID 1482489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.[AlH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:9][NH2:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 24276601HCID 24276601, compound

Product 1

HCID 163948842-(4-Chlorophenyl)-2-(pyrrolidin-1-yl)ethan-1-amineYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-Chloro-phenyl)-pyrrolidin-1-yl-acetonitrile (3.52 g, 15.2 mmol; in Tetrahydrofuran (96 mL) was added Lithium tetrahydroaluminate (1225 mg, 32.28 mmol) and the reaction was refluxed over night. The reaction was quenched with H2O (1.22 ml), 2M NaOH (aq) (1.22 ml) and H2O (2.44 ml). The solid was filtered off and the reaction was concentrated, to yield 2-(4-chlorophenyl)-2-(pyrrolidin-1-yl)ethanamine (1.14 g, 30% yield).

Workup

  1. temperaturethe reaction was refluxed over night
  2. customThe reaction was quenched with H2O (1.22 ml), 2M NaOH (aq) (1.22 ml) and H2O (2.44 ml)
  3. filtrationThe solid was filtered off
  4. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-937bbc49f263452f84d3852305dc15bb
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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