(1,1'-Biphenyl)-4-carboxylic acid → HCID 16812804, compound

HRID 1913149Notes

Reaction equation

HRID 1913149 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]2[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=2)[CH2:18][CH2:17]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.C([O-])(O)=O.[Na+].O>[NH:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[CH:19]1[CH2:20][CH2:21][N:16]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:6][CH:5]=2)=[O:9])[CH2:17][CH2:18]1

Participants

8

Reactant 3

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 7158102-(piperidin-4-yl)-1H-1,3-benzodiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 16812804HCID 16812804, compoundYield 73.2%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 4-biphenyl carboxylic acid (10.0 g, 50.5 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole (10.1 g, 50.5 mmol) in DCM (400 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.0 g, 62.7 mmol) and 4-dimethylaminopyridine (3.08 g, 25.2 mmol). After 3 h the reaction mixture is diluted with saturated aqueous NaHCO3 (200 mL) and water (100 mL). The mixture is stirred for a few minutes. The organic layer is separated, washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration with EtOAc and further washing with EtOAc gives 14.1 g of [4-(1H-benzimidazol-2-yl)piperidin-1-yl](biphenyl-4-yl)methanone.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washTrituration with EtOAc and further washing with EtOAc

Sources & evidence

ORD record
ord-327e6c11082f4b369262b10e15821286
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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