Ammonia → HCID 20338073, compound

HRID 1395768Notes

Reaction equation

HRID 1395768 reaction equation
C(Cl)Cl.[N:4]1[C:14]2[O:13][C:12]3[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:18][C:11]=3[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.C1([N:30]=C=NC2CCCCC2)CCCCC1.N>C(O)(=O)C>[N:4]1[C:14]2[O:13][C:12]3[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[C:20]([NH2:30])=[O:21])=[CH:18][C:11]=3[CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 20338048HCID 20338048, compound

Product 1

HCID 20338073HCID 20338073, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 10 ml of methylene chloride solution containing 50 mg of 2-(5,6-dihydro benzo[b]pyrido[3,2-f]oxepin-8-yl)-propionic acid and 50 mg of dicyclohexylcarbodiimide was added 5 ml of methylene chloride saturated with ammonia, and the mixture was stirred with ice-cooling for 2 hours. To this were added acetic acid and ice and the resulting mixture was extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution, then saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the residue, which was extracted with ethyl acetate and the extract was freed of the solvent. The resulting residue was chromatographed over silica gel, eluted with n-hexane/acetone (4/1-1/1), and there was obtained 22 mg of 2-(5,6-dihydro benzo[b]pyrido[3,2-f]oxepin-8-yl)-propionamide as white crystals. These were recrystallized from ethyl acetate to give colorless crystals having a melting point of 162°-165° C.

Workup

  1. temperaturecooling for 2 hours
  2. extractionthe resulting mixture was extracted with chloroform
  3. washThe extract was washed with saturated sodium hydrogencarbonate solution
  4. dry with materialsaturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain the residue, which
  7. extractionwas extracted with ethyl acetate
  8. customThe resulting residue was chromatographed over silica gel
  9. washeluted with n-hexane/acetone (4/1-1/1)

Sources & evidence

ORD record
ord-220b00c2e6da4b06b76028a17f8a5b84
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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