Acetic Acid → HCID 9843596, compound

HRID 1016290Notes

Reaction equation

HRID 1016290 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH2:21]([N:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C>CO.ClCCl>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[C:31]2[CH2:32][CH2:33][N:28]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:29][CH:30]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 146245-BenzyloxyindoleHCID 192201-Benzyl-4-piperidoneHCID 10942334Sodium Methoxide

Product 1

HCID 9843596HCID 9843596, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A slurry of 5-benzyloxyindole (6.85 g, 30.7 mmol) in methanol (50 mL) was added to a 25 wgt % solution of sodium methoxide in methanol (115 mL) at 5° C. under argon. 1-Benzyl-4-piperidone (5.8 g, 30.7 mmol) was added in one portion and the suspension heated at reflux for 16 h, cooled and diluted with a mixture of dichloromethane (100 mL) and methanol (150 mL). The solution was acidified to pH 5 with glacial acetic acid, concentrated to 100 mL, diluted with water (750 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL) and dried (Na2SO4). Filtration and concentration in vacuo gave the title compound as a yellowrange solid (10.6 g, 87%). MS(ES) m/e 395.2 [M+H]+.

Workup

  1. temperaturethe suspension heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. concentrationconcentrated to 100 mL
  5. additiondiluted with water (750 mL)
  6. extractionextracted with ethyl acetate (3×200 mL)
  7. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-b679b78762f14e8e8330d75f8825e320
Source dataset
uspto-grants-2002_11
Patent number
US06476028B1

Reaction notes

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