4-Benzylpiperidine → HCID 69420844, compound

HRID 1357043Notes

Reaction equation

HRID 1357043 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:12]([OH:14])=O)=[CH:5][C:6]2[NH:10][CH:9]=[N:8][C:7]=2[CH:11]=1.CC[N:17]=C=NCCCN(C)C.Cl.[CH2:27]([CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([C:12]([NH2:17])=[O:14])=[CH:5][C:6]2[NH:10][C:9]([N:37]3[CH2:38][CH2:39][CH:34]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:35][CH2:36]3)=[N:8][C:7]=2[CH:11]=1

Participants

6

Reactant 3

HCID 317384-BenzylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 185048955-Methoxy-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 69420844HCID 69420844, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

6-methoxy-5-benzimidazole carboxylic acid, (1 equivalent) was treated with 1.1 equivalent of EDAC.HCl and 1 equivalent of 4-benzylpiperidine in the presence of a catalytic amount of DMAP in DMF/DCM 1:1 for 3-6 hrs. The reaction mixture was then concentrated and taken up in ethyl acetate. After washing with 5% aq. Sodium carbonate and a solution of saturated sodium chloride, the organic layer was dried over anhydrous sodium sulfate and concentrated to give crude material. This crude material was purified by chromatography on silica. M+ 349, Exp. 349.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. washAfter washing with 5% aq. Sodium carbonate
  3. dry with materiala solution of saturated sodium chloride, the organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give crude material
  6. customThis crude material was purified by chromatography on silica

Sources & evidence

ORD record
ord-e3a26c0ff6f34920b9bbea0de0aa0ed9
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

Loading…