Aluminium lithium hydride → 3-(3-Chlorophenyl)propan-1-amine

HRID 2117601Notes

Reaction equation

HRID 2117601 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]([NH2:18])=O)[CH:11]=[CH:12][CH:13]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][NH2:18])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride3×HCID 534396243-(3-Chlorophenyl)prop-2-enamide

Product 1

HCID 222468753-(3-Chlorophenyl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of LiAlH4 in THF (6.0 mL) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide prepared of Preparation 12, Step A (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An additional 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H), 7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1).

Workup

  1. stirringthe reaction was stirred for 18 h
  2. stirringthe reaction was stirred for 24 h
  3. customThe reaction mixture was quenched by dropwise addition of water
  4. concentrationThe mixture was concentrated in vacuo
  5. customto remove THF
  6. additionwas diluted with water
  7. extractionThe aqueous solution was extracted with EtOAc
  8. washThe organic solution was washed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. dissolutionThe residue was dissolved in CHCl3
  13. washthe organic solution was washed with 1M HCl
  14. extractionthe product was extracted into CHCl3
  15. dry with materialThe organic solution was dried over MgSO4
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6335b86df4b64aa8804b5dc8b3713d64
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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