tert-Butyl 4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidine-1-carboxylate → 3-isopropyl-2-oxo-N-(piperidin-4-ylmethyl)-2,3-dihydro-1H-benzimidazole-1-carboxamide

HRID 16595Notes

Reaction equation

HRID 16595 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[O:14])[C:5]1=[O:30])([CH3:3])[CH3:2]>Cl.CO>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[O:14])[C:5]1=[O:30])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59428174tert-Butyl 4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidine-1-carboxylate

Product 1

HCID 442491883-isopropyl-2-oxo-N-(piperidin-4-ylmethyl)-2,3-dihydro-1H-benzimidazole-1-carboxamideYield 75%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidine-1-carboxylate (3.992 g, 9.58 mmol) in 50 ml 10% hydrochloric acid in methanol and 10 ml concentrated hydrochloric acid was stirred at room temperature for 18 hours. The mixture was then concentrated and basified with aqueous Na2CO3, extracted with CHCl3 (100 ml) for 3 times. The combined extract was dried and concentrated. Flash chromatography of the residue (NH-silica gel, elutent: CH2Cl2/methanol=100/1) afforded a colorless oil 2.272 g (75%) as the title compound.

Workup

  1. concentrationThe mixture was then concentrated
  2. extractionextracted with CHCl3 (100 ml) for 3 times
  3. extractionThe combined extract
  4. customwas dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d51d06c29844231b01d703a69855721
Source dataset
uspto-grants-2010_06
Patent number
US07737163B2

Reaction notes

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