Hydrochloric Acid → HCID 18472660, compound

HRID 2228145Notes

Reaction equation

HRID 2228145 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[CH2:26][CH2:27][O:28][C:29]3[CH:35]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)=[CH:32][C:30]=3[CH:31]=2)=[O:24])=[CH:18][CH:17]=1)=[O:15])=O)(C)(C)C.Cl>CO.C(OCC)(=O)C>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([C:25]2[CH2:26][CH2:27][O:28][C:29]3[CH:35]=[CH:34][C:33]([C:36]4[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=4)=[CH:32][C:30]=3[CH:31]=2)=[O:24])=[CH:20][CH:21]=1)=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18472547HCID 18472547, compound

Product 1

HCID 18472660HCID 18472660, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In methanol (100 ml) and ethyl acetate (150 ml) was dissolved N-(4—(1—(tert-butoxycarbonyl)piperidin-2-ylcarbonyl)phenyl)-7—(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (1.0 g), and to the mixture was added hydrochloric acid (17 ml). The mixture was stirred at room temperature for 2 hours, concentrated and neutralized with sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give crude crystals, which were recrystallized from ethanol-ethyl acetate-hexane to give N-(4—(piperidin-2-ylcarbonyl)phenyl)-7—(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 156) (0.6 g) as colorless crystals.

Workup

  1. concentrationconcentrated and neutralized with sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customto give crude crystals, which
  7. customwere recrystallized from ethanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-8fea9d9f3e3a4d2f9e77feceae20b9cb
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

Loading…