Carbon Dioxide → Hexahydro-2,5-methanopentalene-3a[1H]-carboxylic acid 2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl ester

HRID 2351544노트

반응식

HRID 2351544 반응식
[CH2:1]1[CH:8]2[C:4]3([C:10]([OH:12])=[O:11])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][N:39]([CH2:42][CH2:43]O)[CH2:38][CH2:37]1>C(Cl)(Cl)Cl>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:37][CH2:38][N:39]([CH2:42][CH2:43][O:11][C:10]([C:4]23[CH2:5][CH:6]4[CH2:9][CH:2]([CH2:1][CH:8]2[CH2:7]4)[CH2:3]3)=[O:12])[CH2:40][CH2:41]1

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acidHCID 111073541-Piperazineethanol, 4-(2-methoxyphenyl)-

생성물 1

HCID 4742716Hexahydro-2,5-methanopentalene-3a[1H]-carboxylic acid 2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl ester

시약·촉매·용매 1

HCID 6212Chloroform용매3회

실험 절차

To a stirred solution of hexahydro-2,5-methanopentalene-3a[1H]-carboxylic acid (0.6 g, 3.6×10-3 mol) in 25 ml of chloroform un der a dry nitrogen atmosphere was added carbonyldiimidazole (0.58 g, 3.6×10-3 mol). The resulting solution was stirred at ambient temperature for three hours, during which time a gas (CO2) was evolved. A solution of 2-[1-(2-methoxyphenyl)-4-piperazinyl]ethanol (0.86 g, 3.6×10-3 mol) in 25 ml of chloroform was then added, and the resulting reaction mixture was stirred under nitrogen at ambient temperature for two days. The mixture was diluted to 150 ml with chloroform, washed with three-one hundred ml portions of water, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The desired product (TLC on silica using a 30% methanol in ethyl acetate solvent system, RF=0.60) was isolated by gravity chromatography on silica gel and converted to the hydrochloride salt with isopropanolic HCl (0.82 g, 44% yield), mp.=207°-208° C.

후처리

  1. customthe resulting reaction mixture
  2. washwashed with three-one hundred ml portions of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-73df35b8540d4ec18326f427088b34b3
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04873331

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