Water → (3-Cyclopropyl-4-fluorophenyl)methanamine

HRID 401794Notes

Reaction equation

HRID 401794 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=2[F:13])[C:7]([NH2:9])=O)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH2:7][NH2:9])[CH:10]=[CH:11][C:12]=2[F:13])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 401517983-Cyclopropyl-4-fluorobenzamide

Product 1

HCID 40151800(3-Cyclopropyl-4-fluorophenyl)methanamineYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-cyclopropyl-4-fluoro-benzamide (Preparation 57, 66 g, 0.37 mol, 1.0 eq) in THF (500 mL) was added portionwise lithium aluminium hydride (42 g, 1.1 mol, 3.0 eq) at 10° C. Then the mixture was stirred at room temperature overnight. Water (100 mL) was added dropwise to the reaction mixture at 10° C. and the mixture was filtrated. The solid was washed with THF (3×700 mL), and filtrate was dried over sodium sulfate and concentrated in vacuum to give crude. The crude product was purified by column chromatography (MeOH/DCM 1:100→1:40) to give title compound as a yellow liquid (42.27 g, 0.257 mol, 69.5%).

Workup

  1. filtrationthe mixture was filtrated
  2. washThe solid was washed with THF (3×700 mL), and filtrate
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customto give crude
  6. customThe crude product was purified by column chromatography (MeOH/DCM 1:100→1:40)

Sources & evidence

ORD record
ord-e010d2d920c14a469ac51a4042d8d1e6
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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