Triethylamine → 2-Trifluoromethyl-10-[3-(4-beta-{2-methylheptanoyloxy}ethoxypiperidino)-propyl]-phenothiazine

HRID 329045

Reaction equation

HRID 329045 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([O:26][CH2:27][CH2:28][OH:29])[CH2:22][CH2:21]3)[C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH3:39][CH:40]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:41](Cl)=[O:42]>C1C=CC=CC=1>[F:31][C:2]([F:30])([F:1])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH:23]([O:26][CH2:27][CH2:28][O:29][C:41](=[O:42])[CH:40]([CH3:39])[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:24][CH2:25]3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218089FlupimazineHCID 142345192-Methylheptanoyl chloride

Product 1

HCID 537215472-Trifluoromethyl-10-[3-(4-beta-{2-methylheptanoyloxy}ethoxypiperidino)-propyl]-phenothiazineYield 30%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

13.55 g of 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine (prepared by Example XLIII), 5.4 ml of triethylamine and 100 ml of anhydrous benzene were added to a flask and a solution of 5.7 g of 2-methyl-heptanoic acid chloride in 50 ml of anhydrous benzene was added thereto. The mixture was agitated at room temperature for 24 hours and then the precipitate formed was removed by filtration. The benzene filtrate was washed with an aqueous solution of sodium bicarbonate, then with water. After drying and concentration of the benzene solution, the resulting oil was purified by chromatography on silica gel. After elution with ethanol and evaporation of the solvent, 5.2 g of 2-trifluoromethyl-10-[3-(4-β-{2-methylheptanoyloxy}ethoxypiperidino)-propyl]-phenothiazine as a clear oil were obtained.

Workup

  1. customthe precipitate formed
  2. customwas removed by filtration
  3. washThe benzene filtrate was washed with an aqueous solution of sodium bicarbonate
  4. customAfter drying
  5. customconcentration of the benzene solution, the resulting oil was purified by chromatography on silica gel
  6. washAfter elution
  7. customwith ethanol and evaporation of the solvent

Sources & evidence

ORD record
ord-f1c30b42051d48ec83d999ce52d27245
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Linked notes

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