Water → HCID 54031537, compound

HRID 457761Notes

Reaction equation

HRID 457761 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-b925ce5b554d47b493a6fe3fa7417e03
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

Loading…