Water → HCID 178468978, 화합물

HRID 351542

반응식

HRID 351542 반응식
[CH:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)=[O:18])[CH3:15].C([BH3-])#N.[Na+].O>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([N:28]3[CH2:27][CH2:26][N:25]([C:22]4[CH:21]=[CH:20][C:19]([C:17]([O:16][CH2:14][CH3:15])=[O:18])=[CH:24][CH:23]=4)[CH2:30][CH2:29]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 962WaterHCID 41690(1,1'-Bicyclohexyl)-4-oneHCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 178468978HCID 178468978, 화합물수율 20.3%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매

실험 절차

A mixture of 4-cyclohexylcyclohexanone (1.54 g), 1-(4-ethoxycarbonylphenyl)piperazine (2 g) and titanium(IV) isopropoxide (3.18 ml) was stirred at room temperature. After 1 hour, the IR spectrum of the mixture showed no ketone band, and the viscous solution was diluted with absolute ethanol (8.5 ml). Sodium cyanoborohydride (0.343 g) was added, and the solution was stirred for 3 hours. Water (3 ml) was added with stirring, and the resulting in organic precipitate was filtered and washed with ethanol. The filtrate was extracted with ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane/ethyl acetate)=(3/1). The fractions containing the less polar compound were collected and evaporated under reduced pressure to give ethyl 4-[4-(cis-4-cyclohexylcyclohexyl)piperazin-1-yl]benzoate (692 mg) as byproduct. The fractions containing the more polar compound were collected and evaporated under reduced pressure to give ethyl 4-[4-(trans-4-cyclohexylcyclohexyl)piperazin-1-yl]benzoate (587 mg).

후처리

  1. stirringthe solution was stirred for 3 hours
  2. stirringwith stirring
  3. filtrationthe resulting in organic precipitate was filtered
  4. washwashed with ethanol
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. customfiltrate was evaporated under reduced pressure
  9. washeluted with (hexane/ethyl acetate)=(3/1)
  10. additionThe fractions containing the less polar compound
  11. customwere collected
  12. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-9d9de2240edd40cca52a14699746cbfa
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743776B2

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