Water → 2,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylate

HRID 128639

반응식

HRID 128639 반응식
[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][N:22](C)[CH2:21][CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].[Cl:26][C:27]([Cl:34])([Cl:33])[CH2:28][O:29][C:30](Cl)=[O:31].O>C1C=CC=CC=1>[CH2:1]([C:4]1([C:19]2[CH2:24][CH2:23][NH:22][CH:21]([C:30]([O:29][CH2:28][C:27]([Cl:34])([Cl:33])[Cl:26])=[O:31])[CH:20]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 870632,2,2-Trichloroethyl chloroformateHCID 97975634-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine

생성물 1

HCID 214741302,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylate수율 75.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Dissolved 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1-methyl-1,2,5,6-tetrahydropyridine (3.3 g, 10.0 mmol) in 50 mL of benzene, and added 2,2,2-trichloroethylchloroformate (3.0 mL, 4.6 g, 21.8 mmol). Refluxed for 20 hours under a nitrogen atmosphere. Cooled to room temperature, and added water. Extracted with ether. Dried combined organic extracts with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with dichloromethane. Combined appropriate fractions, and evaporated to give 3.7 g (75% yield) of 2,2,2-trichloroethyl 4-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-1,2,5,6-tetrahydro-pyridinecarboxylate as an oil.

후처리

  1. temperatureRefluxed for 20 hours under a nitrogen atmosphere
  2. extractionExtracted with ether
  3. customDried
  4. filtrationfiltered
  5. customevaporated
  6. customPurified crude product by flash chromatography on silica gel eluting with dichloromethane
  7. customevaporated

출처 및 근거

ORD 기록
ord-06d7e06d6715425dafa4f7b7b6d3def6
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464840

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