Dimethylformamide → HCID 19857986, compound

HRID 2073293Notes

Reaction equation

HRID 2073293 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(O)=O)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH:21]=1.CN([CH:34]=[O:35])C>ClCCl>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:34]([C:15]2[C:10]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:35])[CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 72927Pyridine, 3-(4-aminobutyl)-

Product 1

HCID 19857986HCID 19857986, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 5.0 g of biphenyl-4-carboxylic acid in 20 mL of dichloromethane and 0.5 mL of DMF was treated with 2.1 mL of thionyl chloride and the resulting mixture was heated to reflux until a clear solution was obtained. The mixture was cooled to room temperature and 7.8 g of 3-pyridinebutanamine was slowly added. The reaction mixture was stirred for 10 minutes. was diluted with 150 mL of dichloromethane and was washed with 50 mL of 1N sodium hydroxide. The organic layer was dried over potassium carbonate and evaporated and the residue was crystallized from ethyl acetate-hexane with a charcoal treatment to yield 5.0 g (61%) of N-[4-(3-pyridinyl)butyl][1,1'-biphenyl]-carboxamide, mp 122.5°-126° C. The hydrochloride salt was recrystallized from isopropanol-ether, mp 158°-160° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux until a clear solution
  3. customwas obtained
  4. washwas washed with 50 mL of 1N sodium hydroxide
  5. dry with materialThe organic layer was dried over potassium carbonate
  6. customevaporated
  7. customthe residue was crystallized from ethyl acetate-hexane with a charcoal treatment

Sources & evidence

ORD record
ord-ecd425bc26544645a17b4b82eb888427
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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