1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → ethyl 1-(1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

HRID 83650

Reaction equation

HRID 83650 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1>C(Cl)Cl.O.C(OCC)(=O)C>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]([N:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1)=[O:12]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acid

Product 1

HCID 68379598ethyl 1-(1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1H-benzo[d]imidazole-2-carboxylic acid, H2O (500 mg, 2.78 mmol), EDCI (1170 mg, 6.11 mmol), and 1-HYDROXYBENZOTRIAZOLE (825 mg, 6.11 mmol) were dissolved in DCM. The reaction was allowed to stir for 10 minutes before Hunig's Base (1.066 mL, 6.11 mmol) and ethyl piperidine-4-carboxylate (0.941 mL, 6.11 mmol) were added. The reaction was allowed to stir overnight at room temperature. The reaction was diluted with water and ethyl acetate. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride solution. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The resulting crude material was triturated with ethyl acetate to obtain white solid as a product. (Yield: 113 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 13.09, 7.74, 7.53, 7.36-7.20, 5.31, 4.42, 4.09, 3.48, 3.05, 2.77-2.66, 1.97, 1.69-1.50, 1.20

Workup

  1. additionwere added
  2. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride solution
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude material was triturated with ethyl acetate
  7. customto obtain white solid as a product

Sources & evidence

ORD record
ord-e1197e1bdd544ebba4deaa7ef24d5c7b
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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