1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl (1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

HRID 582069Notes

Reaction equation

HRID 582069 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]2[O:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:12]=2)[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[N:3]=1.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]1.N12CCCN=C1CCC[CH2:36][CH2:35]2>N1C=CC=CC=1>[CH2:35]([N:22]([C:2]1[N:6]([CH2:7][C:8]2[O:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:12]=2)[C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]=2[N:3]=1)[CH:23]1[CH2:24][CH2:25][N:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH2:28]1)[CH3:36]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 184649721-(5-(ethoxycarbonyl)fur-2-ylmethyl)-2-chloro-1H-benzimidazole

Product 1

HCID 131721308ethyl (1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2-chloro-1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazole (9.50 g, 31.2 mmol) and ethyl 4-aminopiperidine-1-carboxylate (5.4 g, 31 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (5.6 mL, 37.4 mmol), and pyridine (90 mL). Heat to reflux. After 18 hours, cool to ambient temperature and evaporate in vacuo to give ethyl (1-(5-ethyoxycarbonylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine.

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo

Sources & evidence

ORD record
ord-92fac21226b54ca0806b50e33a7b8508
Source dataset
uspto-grants-1999_07
Patent number
US05922737

Reaction notes

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