Water → HCID 13769175, compound

HRID 2232518Notes

Reaction equation

HRID 2232518 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]([OH:26])=O)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].O>C(Cl)(Cl)Cl>[CH2:27]([N:29]([CH2:30][CH3:31])[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:20]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 13769232HCID 13769232, compound

Product 1

HCID 13769175HCID 13769175, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

Thionyl chloride (1.02 cc) is added to a solution of 2-phenyl-4-quinolinebutanoic acid (3.7 g) in chloroform (60 cc), and the mixture is heated under reflux for 15 minutes. The solvents are evaporated off under reduced pressure. The residue obtained is dissolved in chloroform (40 cc). Diethylamine (6 cc) is added slowly to this solution in the course of 20 minutes. The mixture is stirred for 3 hours at room temperature (approximately 20° C.) and taken up with water (40 cc). The organic phase is decanted, washed with water (40 cc), dried over magnesium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel, using a cyclohexane/ethyl acetate (50:50 by volume) mixture as eluant. N,N-Diethyl-2-phenyl-4-quinolinebutanamide (3.3 g) is thereby obtained, and this is converted to the monohydrochloride in acetone. The hydrochloride melts at 130° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. customThe solvents are evaporated off under reduced pressure
  4. customThe residue obtained
  5. customThe organic phase is decanted
  6. washwashed with water (40 cc)
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-aba1dac20cd84cd485834f441b091566
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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