Sodium hydride → ethyl 4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:16]1[N:20]([CH2:21][CH2:22][O:23][CH2:24][CH3:25])[C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]=2[N:17]=1>CN(C)C=O>[CH2:24]([O:23][CH2:22][CH2:21][N:20]1[C:19]2[CH:26]=[CH:27][CH:28]=[CH:29][C:18]=2[N:17]=[C:16]1[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)[CH3:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred mixture of 34.64 parts of ethyl 4-hydroxy-1-piperidinecarboxylate and 940 parts of N,N-dimethylformamide were added portionwise 10 parts of a sodium hydride dispersion 50% at room temperature under nitrogen atmosphere. Upon complete addition, stirring was continued for 1 hour at room temperature. A solution of 45 parts of 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole in N,N-dimethylformamide was added dropwise at 50° C. Upon completion, the whole was stirred overnight at 50° C. The reaction mixture was poured into ice water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated, yielding 50 parts (69.1%) of ethyl 4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]oxy]-1-piperidinecarboxylate as a residue (compound 19).
Workup
- additionUpon complete addition
- stirringUpon completion, the whole was stirred overnight at 50° C
- extractionthe product was extracted with trichloromethane
- customThe extract was dried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-69c724cea0e7415098414226946ed5c1
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04943580
Reaction notes
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