1,1'-Carbonyldiimidazole → HCID 14556122, compound

HRID 364637Notes

Reaction equation

HRID 364637 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][CH:26]1[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1>O1CCCC1>[N:28]12[CH2:33][CH2:32][CH:31]([CH2:30][CH2:29]1)[CH:26]([NH:25][C:10]([C:6]1[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]3)=[O:12])[CH2:27]2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 742801H-Indole-5-Carboxylic AcidHCID 1232383-Aminoquinuclidine

Product 1

HCID 14556122HCID 14556122, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (50 ml) was added to a mixture of indole-5-carboxylic acid (2.42 g, 0.016 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole). The mixture was stirred for 1 hr while nitrogen was bubbled through the solution to remove the carbon dioxide that was evolved. Then 3-aminoquinuclidine (1.89 g, 0.015 mole) was added in one portion, and the mixture was stirred for 60 hr at room temperature. The solid product was collected by filtration to yield 3.75 g (86.8%). Recrystallization from methanol-isopropyl ether (with chilling) gave 1.89 g of the product as an off-white solid; m.p. 293°-295° C. The solid was vacuum dried at 82° C. for 16 hr, m.p. 293°-295° C.

Workup

  1. customwas bubbled through the solution
  2. customto remove the carbon dioxide that
  3. stirringthe mixture was stirred for 60 hr at room temperature
  4. filtrationThe solid product was collected by filtration
  5. customto yield 3.75 g (86.8%)
  6. customRecrystallization from methanol-isopropyl ether (with chilling)

Sources & evidence

ORD record
ord-1de43a7f9019420984aeef3a18cb6860
Source dataset
uspto-grants-1986_08
Patent number
US04605652

Reaction notes

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