4-(4-Chlorophenyl)butanamide → 4-(4-Chlorophenyl)butan-1-amine

HRID 1021393Notes

Reaction equation

HRID 1021393 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([NH2:19])=O)=[CH:10][CH:9]=1>C(OCC)C.O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:19])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 110743574-(4-Chlorophenyl)butanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 107738224-(4-Chlorophenyl)butan-1-amineYield 61%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (1.84 g, 48.6 mmol) in diethyl ether (50 mL) at ambient temperature was added a solution of 4-(4-chlorophenyl)butanamide in tetrahydrofuran (25 mL), dropwise over 8 minutes. Stirring was continued at ambient temperature for a further 4 hours. The reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL). After stirring the mixture for 20 minutes, it was extracted with diethyl ether (50 mL). The organic layer was dried over sodium sulfate and concentrated to afford 4-(4-chlorophenyl)butan-1-amine as a light yellow oil (1.36 g, 61%).

Workup

  1. waitwas continued at ambient temperature for a further 4 hours
  2. customThe reaction mixture was carefully quenched by sequential slow addition of water (2 mL), 10M sodium hydroxide (0.75 mL), and water (7 mL)
  3. stirringAfter stirring the mixture for 20 minutes
  4. extractionit was extracted with diethyl ether (50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b16e619b081e43e1b797b1a2abaa452b
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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