1,1'-Carbonyldiimidazole → 2,3,4,9-Tetrahydro-1h-carbazole-6-carboxamide

HRID 566614

반응식

HRID 566614 반응식
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([C:14]([OH:16])=O)=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)([N:19]1C=CN=C1)=O.ClC1C(Cl)=CC=CC=1N1CCN(CCCCN)CC1>O1CCCC1>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([C:14]([NH2:19])=[O:16])=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7298012,3,4,9-tetrahydro-1H-carbazole-6-carboxylic acidHCID 110986691-Piperazinebutanamine, 4-(2,3-dichlorophenyl)-

생성물 1

HCID 2441832,3,4,9-Tetrahydro-1h-carbazole-6-carboxamide수율 163.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 1,2,3,4-tetrahyrocarbazole-6-carboxylic acid (100 mg, 0.46 mmol) and 1,1′-carbonyldiimidazole (78 mg, 0.48 mmol) in 5 mL of anhydrous tetrahydrofliran was stirred for 8 hours. A solution of 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-aminobutane (140 mg, 0.46 mmol) in 1 mL of tetrahydrofuran was added and the resulting mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous Na2CO3 solution, dried (Na2SO4) and concentrated in vacuo to afford the free base of the title compound, N-(1-{4-[4-2,3-dichlorophenyl)piperazin-1-yl]}butyl)-1,2,3,4-tetrahydrocarbazole-6carboxamide, (161 mg, 70%). The hydrochloride salt was prepared by treating the free base with a solution of hydrogen chloride in ethyl acetate (mp 236-238° C.).

후처리

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous Na2CO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-387532280d2c458983d300677c9b313f
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06175015B1

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