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

HRID 566614

反応式

HRID 566614 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-387532280d2c458983d300677c9b313f
出典データセット
uspto-grants-2001_01
特許番号
US06175015B1

関連ノート

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