Sodium Chloride → 4-Benzyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine

HRID 2304277Notes

Reaction equation

HRID 2304277 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydride2×HCID 22665722HCID 22665722, compound

Product 1

HCID 226659024-Benzyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepineYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 g of 4-benzyl-4,5-dihydro-benzo[f][1,4]oxazepin-3-one in 50 mL of tetrahydrofuran was added dropwise to a suspension of 1.14 g of lithium aluminum hydride in 50 mL of tetrahydrofuran. The mixture was refluxed for 5 hours and then allowed to cool down to room temperature. 2.2 mL of saturated aqueous sodium chloride solution was added in order to decompose excess lithium aluminum hydride. The precipitated solid was removed by filtration, and the filtrate was concentrated to give 2.2 g of pure 4-benzyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine as an oil. EI-MS: 239 (M+).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customThe precipitated solid was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-49086b6b13d1422dafa682b10a13653b
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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