4-Phenylbutyric Acid → HCID 9859422, compound

HRID 1614559Notes

Reaction equation

HRID 1614559 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:13]1[CH2:18][CH:17]=[CH:16][CH2:15][CH2:14]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([N:13]2[CH2:14][CH:15]=[CH:16][CH2:17][CH2:18]2)=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 47754-Phenylbutyric AcidHCID 127501,2,3,6-TetrahydropyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9859422HCID 9859422, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 mmol of 4-phenyl butyric acid, 5 mmol of 1,2,3,6-tetrahydropyridine, and 6 mmol of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were mixed with 20 ml of methylene chloride. The mixture was reacted for 2 hours at room temperature with stirring. The reaction mixture was washed with 5% hydrochloric acid, 2% sodium hydroxide, and brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel to obtain 950 mg of colorless crystals of N-(4-phenylbutanoyl)-1,2,3,6-tetrahydropyridine (yield: 83%).

Workup

  1. customThe mixture was reacted for 2 hours at room temperature
  2. washThe reaction mixture was washed with 5% hydrochloric acid, 2% sodium hydroxide, and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b41991d38baa4a6ba731a89362d70e48
Source dataset
uspto-grants-1993_03
Patent number
US05198450

Reaction notes

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