Ethanol → HCID 18332987, compound

HRID 2269720Notes

Reaction equation

HRID 2269720 reaction equation
[H-].[Na+].C(O)C.[C:6]([CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])([O:8][CH2:9][CH3:10])=[O:7].[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br)([O-:20])=[O:19]>O>[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][C:11]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 977733-Carbethoxy-2-piperidone

Product 1

HCID 18332987HCID 18332987, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil, 2.45 g) was added to ethanol (100 ml), to which was added 3-carboethoxy-2-piperidone (10.0 g). The reaction mixture was stirred for 15 minutes, to which was added 2-nitrobenzyl bromide (13.2 g) at room temperature. The reaction mixture was stirred at 60° C. for 3 hours. Water was added to the reaction mixture, which was concentrated. The residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (14.6 g).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 3 hours
  2. concentrationwas concentrated
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated
  8. customThe obtained crude crystals
  9. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5d6b7880a5f6456c8ce13d06b61535fd
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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