Sodium Bicarbonate → HCID 22492878, compound

HRID 1816342Notes

Reaction equation

HRID 1816342 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:18]=[C:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C.O>[CH2:18]=[C:19]1[CH2:24][CH2:23][CH:22]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=3)[CH2:6][CH2:5]2)[CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5734894-MethylenecyclohexanoneHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22492878HCID 22492878, compoundYield 49.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-(piperazinyl)benzoate (2.00 g) and 4-methylenecyclohexan-1-one (0.98 g) in a mixture of methanol (40 ml) and acetic acid (1.47 ml) was portionwise added sodium cyanoborohydride (644 mg) with stirring under ice-cooling and the mixture was stirred at ambient temperature overnight. To the reaction mixture was added water (200 ml) and the mixture was adjusted to pH 8-9 with saturated aqueous sodium hydrogen carbonate. The resulting precipitates were collected and chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (2:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give ethyl 4-[4-(4-methylenecyclohexyl)-1-piperazinyl]benzoate (1.39 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at ambient temperature overnight
  3. customThe resulting precipitates
  4. customwere collected
  5. customchromatographed on silica gel (200 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (2:1 v/v)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-75386e0214b34c488da057aa73feeb0d
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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