1,1'-Carbonyldiimidazole → NGB 2904 hydrochloride

HRID 2258078Notes

Reaction equation

HRID 2258078 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](O)=[O:15].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])[CH2:39][CH2:38]1>O1CCCC1>[ClH:29].[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]1[CH2:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:14]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C:13]=3[CH:1]=2)=[O:15])[CH2:41][CH2:42]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3485919H-fluorene-2-carboxylic acidHCID 110986691-Piperazinebutanamine, 4-(2,3-dichlorophenyl)-

Product 1

HCID 19366304NGB 2904 hydrochlorideYield 139.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 9H-fluorene-2-carboxylic acid (100 mg, 0.48 mmol) and 1,1'-carbonyldiimidazole (80 mg, 0.5 mmol) in 10 mL of anhydrous tetrahydrofuran was 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 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 give the title compound (185 mg, 78%). Hydrochloride salt was prepared lay treating the free base with a solution of hydrogen chloride in ethyl acetate (top 262-4° 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-385f0161e99f4bf781a4ae6f4f2e7f7f
Source dataset
uspto-grants-1997_08
Patent number
US05659033

Reaction notes

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