Potassium Carbonate → HCID 68511203, compound

HRID 1716424Notes

Reaction equation

HRID 1716424 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:15]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 68511203HCID 68511203, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 320 mg (1 mmol) of 4-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester in 5 ml of DMF were added 218 mg (1.5 mmol, 1.5 eq.) of (2-chloro-ethyl)-dimethyl-amine hydrochloride and 418 mg (3 mmol, 3 eq.) of K2CO3. Stirring was continued at 60° C. over night. The mixture was poured on water and the product extracted with EtOAc. The organic phases were dried over Na2SO4 and concentration in vacuo afforded crude 4-[3-(2-dimethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester as an off-white solid. This crude material was then dissolved in 5 ml of CH2Cl2 and 1 ml of TFA was added. After 2 hours at RT, the reaction was quenched by addition of aq. NaHCO3 (pH=9), and the product extracted with CH2Cl2. Concentration in vacuo afforded 200 mg (61%) of the title compound as a white solid.

Workup

  1. waitwas continued at 60° C. over night
  2. additionThe mixture was poured on water
  3. extractionthe product extracted with EtOAc
  4. dry with materialThe organic phases were dried over Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-05b8ba49114644ffa63ab8c060f652fc
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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