1,1'-Carbonyldiimidazole → Ethyl 1-(Benzofuran-3-ylacety)-4-piperidinecarboxylate

HRID 430600Notes

Reaction equation

HRID 430600 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([CH2:22][C:23]([OH:25])=O)=[CH:14]1.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]1>ClCCl>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([CH2:22][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]2)=[O:25])=[CH:14]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70770Ethyl 4-piperidinecarboxylateHCID 27629402-(1-Benzofuran-3-yl)acetic acid

Product 1

HCID 15512383Ethyl 1-(Benzofuran-3-ylacety)-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22 g of carbonyldiimidazole are added in portions to 23.9 g of benzofuran-3-ylacetic acid in 250 ml of dichloromethane. When the evolution of gas has stopped, the reaction mixture is stirred for 1 hour and then 21 ml of ethyl piperid-4-ylcarboxylate are added dropwise. After 12 hours' stirring at room temperature, the reaction mixture is washed with 1N sodium hydroxide solution and then with 1N hydrochloric acid. After decanting and drying, concentration under reduced pressure enables the expected product to be isolated.

Workup

  1. stirringAfter 12 hours' stirring at room temperature
  2. washthe reaction mixture is washed with 1N sodium hydroxide solution
  3. customAfter decanting
  4. customdrying
  5. concentrationconcentration under reduced pressure
  6. customto be isolated

Sources & evidence

ORD record
ord-519d9fcff93846d8911cd7f7fac2334c
Source dataset
uspto-grants-2001_11
Patent number
US06323217B2

Reaction notes

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