Water → 1-Benzyl-4-hydroxyazepane

HRID 1269782Notes

Reaction equation

HRID 1269782 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15143501-Benzyl-hexahydro-4H-azepin-4-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 44295381-Benzyl-4-hydroxyazepaneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-benzyl-4-azepanone (610 mg, 3.00 mmol) in diethyl ether (8 ml) was added to a suspension of lithium aluminum hydride (57 mg, 1.50 mmol) in diethyl ether (5 ml) at 0° C. and stirred for 1 hour. Water (0.057 ml), a 2N-aqueous sodium hydroxide solution (0.114 ml) and then water (0.171 ml) were added to the reaction mixture, and the resulting mixture was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate 1/1, chloroform/methanol=30/1) to obtain 1-benzyl-4-azepanol (516 mg, 84%).

Workup

  1. dry with materialthe resulting mixture was dried over anhydrous magnesium sulfate
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate 1/1, chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-c771e64275094d2ab2cd2bf462e7766e
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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