Chloroacetyl chloride → HCID 13314312, compound

HRID 615314Notes

Reaction equation

HRID 615314 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([OH:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:30][C:31](Cl)=[O:32]>CCOCC>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:12][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:26][CH2:30][C:31]1=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 13314307HCID 13314307, compound

Product 1

HCID 13314312HCID 13314312, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

60 g (0.17 mole) of the N-benzyl-3-hydroxy-3-phenyl-4-phenoxybutylamine obtained as described in (c) were dissolved in 600 ml of ether, 150 ml of 2N sodium hydroxide solution were added and 22.6 g (0.2 mole) of chloroacetyl chloride in 50 ml of ether were added dropwise at room temperature. The mixture was refluxed for 30 minutes, after which the ether phase was separated off and dried, and 150 ml of isopropanol were added. To this solution was added dropwise, in the course of 30 minutes, a solution of 3.4 g of sodium in 375 ml of isopropanol, which solution had been diluted beforehand with 1,200 ml of hexane. The mixture was stirred for 2 hours and then left to stand overnight, after which the solvent was distilled off, water was added and the product was extracted with chloroform. The extract was dried and evaporated down to give 4-benzyl-3-oxo-7-phenyl-7-phenoxymethyl-hexahydro-1,4-oxazepine, which was processed further in crude form.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. customafter which the ether phase was separated off
  3. customdried
  4. addition150 ml of isopropanol were added
  5. additionTo this solution was added dropwise, in the course of 30 minutes
  6. additiona solution of 3.4 g of sodium in 375 ml of isopropanol, which solution had been diluted beforehand with 1,200 ml of hexane
  7. waitleft
  8. waitto stand overnight
  9. distillationafter which the solvent was distilled off
  10. additionwater was added
  11. extractionthe product was extracted with chloroform
  12. customThe extract was dried
  13. customevaporated down

Sources & evidence

ORD record
ord-0bf6ea9c1dfd4567a8ce1fe31a5d5b61
Source dataset
uspto-grants-1985_02
Patent number
US04499087

Reaction notes

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