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

HRID 1578253Notes

Reaction equation

HRID 1578253 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>CCOCC>[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

4

Reactant 2

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

Product 1

HCID 107738224-(4-Chlorophenyl)butan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 12.6 g. (0.33 mole) of lithium aluminum hydride in 340 ml. of dry ether was added dropwise at room temperature 16.4 g. (0.083 mole) of 4-(p-chlorophenyl)-butyramide. The reaction mixture was stirred at room temperature for 4 hours, cooled and cautiously quenched with 13 ml. of water, 10 ml. of 20% sodium hydroxide and 45 ml. of water. The organic layer was separated and the emulsion was extracted with ether. The combined organic and ether extract was dried over sodium hydroxide and concentrated to obtain 4-(p-chlorophenyl)butylamine; m.p. of hydrochloride salt 162°-164° C.

Workup

  1. temperaturecooled
  2. customcautiously quenched with 13 ml
  3. customThe organic layer was separated
  4. extractionthe emulsion was extracted with ether
  5. extractionThe combined organic and ether extract
  6. dry with materialwas dried over sodium hydroxide
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aaa3337d2f4b4f058dbce295fd68e6e1
Source dataset
uspto-grants-1981_09
Patent number
US04292305

Reaction notes

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