1,1'-Carbonyldiimidazole → Ngb-2849

HRID 1418685

Reaction equation

HRID 1418685 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][C:2]=1[C:15](O)=[O:16].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:30][C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=1[N:38]1[CH2:43][CH2:42][N:41]([CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])[CH2:40][CH2:39]1>O1CCCC1>[Cl:30][C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=1[N:38]1[CH2:39][CH2:40][N:41]([CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:15]([C:2]2[CH:3]=[CH:4][C:5]3[C:14](=[CH:13][C:12]4[C:7]([CH:6]=3)=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:1]=2)=[O:16])[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1013252-Anthracenecarboxylic AcidHCID 110986691-Piperazinebutanamine, 4-(2,3-dichlorophenyl)-

Product 1

HCID 15411150Ngb-2849Yield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-anthracenecarboxylic acid (100 mg, 0.45 mmol) and 1,1'-carbonyldiimidazole (82 mg, 0.5 mmol) in 10 mL of anhydrous tetrahydrofuran is stirred for 8 hours. A solution of 4-[4-(2,3-dichlorophenyl)-1-piperazinyl]-1-aminobutane (150 mg, 0.5 mmol) in 1 mL of tetrahydrofuran is added and the resulting mixture is stirred for 30 minutes. The reaction mixture is partitioned between ethyl acetate and water. The organic layer is washed with aqueous Na2CO3, dried (Na2SO4) and concentrated in vacuo to give the title compound (183 mg, 80%). The hydrochloride salt is prepared by treating the free base with ethyl acetate-HCl. The hydrochloride salt of the title compound has a melting point of 245°-247° C.

Workup

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

Sources & evidence

ORD record
ord-88e134f8ad9e4387b33079f45555c6c6
Source dataset
uspto-grants-1999_03
Patent number
US05883257

Linked notes

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