Hydrochloric Acid → HCID 18472660, compound

HRID 565951Notes

Reaction equation

HRID 565951 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 (100ml) and ethyl acetate (150ml) was dissolved N-(4-(1-(tert-butoxycarbonyl)piperidin-2-ylcarbonyl)-phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (1.0g), and to the mixture was added hydrochloric acid (17ml). 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-methyl-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 156) (0.6g) 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-74c1f50ebb8743558368ea749084e79e
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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