Ethyl Acetate → HCID 18538641, compound

HRID 412944Notes

Reaction equation

HRID 412944 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O=C1NC(CN2CCNCC2)=CC(=O)N1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 18538904HCID 18538904, compoundHCID 18539274HCID 18539274, compound

Product 1

HCID 18538641HCID 18538641, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Acetyl-N-(3,4-dichlorophenyl)-N-{3-[4-(4-nitrobenzyl)-1-piperidinyl]propyl}-4-piperidinecarboxamide (Example 302) (70 mg, 0.12 mmol) was dissolved in ethanol (0.4 mL). To the mixture was added stannic chloride 2 hydrate (135 mg, 0.61 mmol), and the mixture was heated for 30 minutes under reflux. The mixture was cooled, and to the mixture were added aqueous solution of 1N-sodium hydroxide (10 mL) and ethyl acetate (10 mL). The resulting white precipitates were filtered off with Celite. The filtrate was subjected to extraction procedure. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (alumina 10 g, ethyl acetate), and the desired fraction was concentrated under reduced pressure to give the titled compound (63 mg, 0.11 mmol, Yield 92%) as pale yellow oily substance.

Workup

  1. temperaturethe mixture was heated for 30 minutes
  2. temperatureunder reflux
  3. temperatureThe mixture was cooled
  4. customThe resulting white precipitates
  5. filtrationwere filtered off with Celite
  6. extractionThe filtrate was subjected to extraction procedure
  7. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-656cfb01e1c849c2b5ac1f4e67091f3e
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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