Sodium hydride → 4-Benzyl-7,7-diphenyl-1,4-oxazepan-3-one

HRID 596164Notes

Reaction equation

HRID 596164 reaction equation
[CH2:1]([N:8]([CH2:13][CH2:14][C:15]([OH:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:14][C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:28][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20326654N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine

Product 1

HCID 203266404-Benzyl-7,7-diphenyl-1,4-oxazepan-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The solution of 19.3 g of N-benzyl-N-chloroacetyl-3hydroxy-3,3-diphenylpropylamine in 150 ml of dimethylformamide is added dropwise to the suspension of 1.2 g of sodium hydride in 50 ml of dimethylformamide while stirring and cooling with an ice-bath. The mixture is allowed to warm up to room temperature, stirred for 15 hours and evaporated. The residue is partitioned between 150 ml methylene chloride and 50 ml of N hydrochloric acid, the organic layer separated, washed with water, dried, filtered and evaporated. The residue is triturated with diethyl ether and recrystallized from ethanol, to yield the 4-benzyl-3-oxo-7,7-diphenyl-hexahydro-1,4-oxazepine of the formula ##STR7## melting at 185° to 186°.

Workup

  1. temperaturecooling with an ice-bath
  2. stirringstirred for 15 hours
  3. customevaporated
  4. customThe residue is partitioned between 150 ml methylene chloride and 50 ml of N hydrochloric acid
  5. customthe organic layer separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated with diethyl ether
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-220e732c0ebe466ebed9812668e1f5d2
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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