Triethylamine → tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

HRID 1716423Notes

Reaction equation

HRID 1716423 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.CCN(CC)CC.[O:24](C(OC(C)(C)C)=O)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:28]([O:27][C:25]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:5][CH2:6]1)=[O:24])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 300 mg (1.4 mmol) of 1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (commercially available) in 15 ml of CH2Cl2 were added 34 mg (0.28 mmol, 0.2 eq.) of DMAP, 190 μl (1.4 mmol, 1 eq.) of Et3N and 301 mg (1.4 mmol, 1 eq.) of (BOC)2O. After stirring at RT overnight the reaction mixture was poured on water and extracted with CH2Cl2. Column chromatography (SiO2, EtOAc/Hept. 1:1) afforded 360 mg (82%) of the title compound as a white solid.

Workup

  1. additionwas poured on water
  2. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-e710b4cccaf343d586b02c7a3005d1f5
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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