1,1'-Carbonyldiimidazole → HCID 19008874, compound

HRID 1742214Notes

Reaction equation

HRID 1742214 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.C(N1C=CN=C1)([N:14]1[CH:18]=[CH:17]N=C1)=O.N1C=C[C:27]([N:30]2[CH2:35][CH2:34][CH:33]([CH2:36][NH2:37])[CH2:32][CH2:31]2)=[N:26][CH:25]=1>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH:37][CH2:36][CH:33]1[CH2:32][CH2:31][N:30]([C:27]2[N:26]=[CH:25][CH:17]=[CH:18][N:14]=2)[CH2:35][CH2:34]1)=[O:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 79139Norborn-2-ylacetic acidHCID 22052431HCID 22052431, compound

Product 1

HCID 19008874HCID 19008874, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-norbornaneacetic acid (1.54 g, 10 mmole) and 1,1'-carbonyldiimidazole (1.62 g, 10 mmole) in methylene chloride (35 ml) was stirred for 15 min and then 1-(4-pyrimidinyl]-4-piperidinemethaneamine (V; 1.92 g, 10 mmole) was added. After stirring for 18 hrs the solution was diluted with methylene chloride (100 ml) and extracted with water (3×30 ml) and saturated sodium carbonate (30 ml). The methylene chloride layer was dried over magnesium sulfate and concentrated in vacuo to give a white solid. The crude product was recrystallized from a mixture of ethyl acetate (15 ml) and hexane (15 ml) to give the formula I product as a white powder (2.59 g, 79%, mp: 121°-126°).

Workup

  1. extractionextracted with water (3×30 ml) and saturated sodium carbonate (30 ml)
  2. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a white solid
  5. customThe crude product was recrystallized from a mixture of ethyl acetate (15 ml) and hexane (15 ml)

Sources & evidence

ORD record
ord-c3f2e30d997540df8817f454bddfee93
Source dataset
uspto-grants-1994_08
Patent number
US05338738

Reaction notes

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