Aluminium lithium hydride → 2-[(4-Chlorophenyl)methyl]azepane

HRID 27437

Reaction equation

HRID 27437 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([CH2:12][CH:13]2[NH:19][C:18](=O)[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 233428517-(4-Chlorobenzyl)perhydroazepin-2-one

Product 1

HCID 39338092-[(4-Chlorophenyl)methyl]azepaneYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 0.5 g of lithium aluminum hydride to a solution of 2.8 g 7-(4-chlorobenzyl)-perhydroazepin -2-one in 30 ml of tetrahydrofurane. Boil the mixture under reflux for 16 hours, cool it and then carefully treat it with ice-water. After extraction with diethyl ether, dry the extract over sodium sulfate concentrate the oily residue and distill in a vacuum to obtain 1.8 g of the title compound with a BP of 90° to 92° at 0.05 mm Hg.

Workup

  1. temperatureBoil the mixture under reflux for 16 hours
  2. temperaturecool it
  3. extractionAfter extraction with diethyl ether
  4. customdry the
  5. extractionextract over sodium sulfate
  6. concentrationconcentrate the oily residue
  7. distillationdistill in a vacuum

Sources & evidence

ORD record
ord-32cc92d9280349b984ea48408cc67dba
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Linked notes

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