Water → 4-Methyl-7,7-diphenyl-1,4-oxazepane

HRID 1288559Notes

Reaction equation

HRID 1288559 reaction equation
[C:1]([N:6]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][CH2:8][CH2:7]1)(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:1][N:6]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20326661HCID 20326661, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 203266324-Methyl-7,7-diphenyl-1,4-oxazepane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.0 g of 4-carbethoxy-7,7-diphenyl-hexahydro-1,4-oxazepine (Example 3) are added portionwise to the suspension of 0.90 g of lithium aluminum hydride in 80 ml of diethyl ether while stirring and cooling with ice. The mixture is allowed to warm up to room temperature, refluxed for 6 hours and again cooled to 0° to 5°. Thereupon 0.9 ml of water, 0.9 ml of 15% aqueous sodium hydroxide and 2.7 ml of water are added in this order, the mixture is filtered, the filtrate dried and evaporated. The residue is taken up in acetone and the solution acidified with cyclohexylsulfamic acid in acetone, to yield the 4-methyl-7,7-diphenyl-hexahydro-1,4-oxazepine melting at 199° to 201°.

Workup

  1. temperaturecooling with ice
  2. temperaturerefluxed for 6 hours
  3. temperatureagain cooled to 0° to 5°
  4. filtrationthe mixture is filtered
  5. customthe filtrate dried
  6. customevaporated

Sources & evidence

ORD record
ord-5f21825b958543929fa9e1e0c843cf65
Source dataset
uspto-grants-1976_10
Patent number
US03988448

Reaction notes

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