Ethanol → HCID 67763789, compound

HRID 362889Notes

Reaction equation

HRID 362889 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([CH:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[CH2:15][O:14][C:13]4[CH:22]=[CH:23][C:24]([Br:26])=[CH:25][C:12]3=4)[CH2:7][CH2:6]2)[O:4]CC1.C(O)C>Cl>[O:4]=[C:5]1[CH2:10][CH2:9][N:8]([CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][O:14][C:13]3[CH:22]=[CH:23][C:24]([Br:26])=[CH:25][C:12]2=3)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 702EthanolHCID 86753734HCID 86753734, compound

Product 1

HCID 67763789HCID 67763789, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Step 2): A suspension of 11-(1,4-dioxa-8-azaspiro[4,5]decane-8-yl)-2-bromo-6,11-dihydrodibenz[b,e]oxepin (5.5 g, 13.2 mmol) in 4N HCl was heated at 60°-70° C. for 30 minutes. Then ethanol was added to the mixture. The mixture was heated at 60°-70° C. for 1.5 hours. After ethanol was evaporated, the reaction mixture was made alkaline with 50% NaOH solution, then extracted with ethyl acetate and chloroform. The organic layer was washed with water, dried (MgSO4) and concentrated to give 11-(4-oxopiperidin-1-yl)-2-bromo-6,11-dihydrodibenz[b,e]oxepin (100%): mp 196°-200° C.

Workup

  1. temperaturewas heated at 60°-70° C. for 30 minutes
  2. temperatureThe mixture was heated at 60°-70° C. for 1.5 hours
  3. customAfter ethanol was evaporated
  4. extractionextracted with ethyl acetate and chloroform
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1ec4ee2f12bd46f5b015c12a2e3e3a30
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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