Water → HCID 54031537, compound

HRID 1357040Notes

Reaction equation

HRID 1357040 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.CC[N:15]=C=NCCCN(C)C.[CH2:24]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:24]([CH:31]1[CH2:36][CH2:35][N:34]([C:2]2[NH:3][C:4]3[CH:9]=[C:8]([C:10]([NH2:15])=[O:12])[CH:7]=[CH:6][C:5]=3[N:1]=2)[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 317384-BenzylpiperidineHCID 4594565-Benzimidazolecarboxylic acid

Product 1

HCID 54031537HCID 54031537, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Benzimidazole-5-carboxylic acid (1.62 g, 10 mMol) was reacted with EDAC (1.92 g, 10 mMol) in 40 mL dry DMF at room temperature for 15 minutes. To the reaction mixture was added 4-benzylpiperidine (1.75 g, 10 mMol) and DMAP (˜20 mg, catalyst) and the mixture was stirred at room temperature for 20 h. It was poured into water and extracted with methylene chloride (3-100 mL). The combined extract was washed with water, brine and again with water. The extract was dried over MgSO4 and evaporated. The residue was chromatographed on a column of silica gel with chloroform-methanol (0 to 5% methanol). Evaporation of the desired fractions gave 1.5 g (47%) of the product after recrystallization from ethyl acetate-hexane. 1HNMR (CDCl3): δ=7.8 (s, 1H); 7.1-7.3 (m, 8H); 4.8-4.7 (broad m, 1H), 3.7-3.9 (broad m, 1H); 3.1-2.7 (broad m, 2H); 2.55 (d, 2H); 2.0-1.1 (m, 5H). MS (ESI) m/e 319 (M+), 318 (M+−H).

Workup

  1. extractionextracted with methylene chloride (3-100 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine and again with water
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on a column of silica gel with chloroform-methanol (0 to 5% methanol)
  7. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-812001bcf013403cbc8c524602a42f99
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

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