1,1'-Carbonyldiimidazole → HCID 67215086, compound

HRID 2421064Notes

Reaction equation

HRID 2421064 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[NH2:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]3[NH:24][C:25]2=[O:26])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67214786HCID 67214786, compound

Product 1

HCID 67215086HCID 67215086, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound {4-(2-aminocyclohexylamino)-piperidine-1-carboxylic acid benzyl ester)} (1.48 g, 4.47 mmoles) in acetonitrile (50 mL), 1,1′-carbonyldiimidazole (0.86 g, 5.36 mmole) was added and the reaction mixture was stirred at room temperature for 18 h. Reaction mixture was concentrated under reduced pressure, dissolved again in dichloromethane (60 mL) washed with water (2×100 mL) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound as a solid (1.45 g, 90%). MS: (M+1): 358.13

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. dissolutiondissolved again in dichloromethane (60 mL)
  4. washwashed with water (2×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-544d133dc0c841d0a2a42adf397dfd9d
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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