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

HRID 514888Notes

Reaction equation

HRID 514888 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-56aa4b0e126b488fa14fb0037972f7aa
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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