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

HRID 566614

Reaction equation

HRID 566614 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-387532280d2c458983d300677c9b313f
Source dataset
uspto-grants-2001_01
Patent number
US06175015B1

Linked notes

Loading…