Dicyclohexylcarbodiimide → HCID 13134791, compound

HRID 355117Notes

Reaction equation

HRID 355117 reaction equation
[N:1]1[C:11]2[O:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([OH:19])=O)=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([N:26]=C=NC2CCCCC2)CCCCC1.N.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[N:1]1[C:11]2[O:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([NH2:26])=[O:19])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 13134789HCID 13134789, compoundHCID 22731429Ammonia dichloromethane

Product 1

HCID 13134791HCID 13134791, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 40 mg of (5,6-dihydro benzo[b]pyrido[3,2-f]-oxepin-8-yl)-acetic acid, 60 mg of dicyclohexylcarbodimide and 2 ml of dry dichloromethane was stirred under ice cooling. To the resulting mixture was added 8 ml of a saturated liquid ammonia-dichloromethane solution, and the mixture was stirred for 3 hours. After the completion of the reaction, this was basified with a saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with water and then with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a light yellow oil, which was chromatographed over 4 g of silica gel and eluted with chloroform/ethyl acetate (10/1-8/2) to obtain crystals. These were recrystallized from ethyl acetate to yield 15 mg (yield: 40%) of (5,6-dihydro benzo[b]pyrido[3,2-f]oxepin-8-yl)-acetamide as light yellow needle crystals having a melting point of 164°-165° C.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialwith a saturated sodium chloride solution and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain a light yellow oil, which
  8. customwas chromatographed over 4 g of silica gel
  9. washeluted with chloroform/ethyl acetate (10/1-8/2)
  10. customto obtain crystals
  11. customThese were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-80a952e3cda4405599c81e82ea3f807e
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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