4-Benzylpiperidine → HCID 69420844, compound

HRID 457764Notes

Reaction equation

HRID 457764 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 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 a solution of saturated sodium chloride
  3. dry with materialthe 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-e711e092f8594141b61b7aba4b70a11a
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

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