Sodium Bicarbonate → 4-(4-fluorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidine

HRID 1193985Notes

Reaction equation

HRID 1193985 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1.Cl[CH2:22][CH2:23][CH2:24][N:25]1[C:38]2[CH:37]=[C:36]([S:39][CH3:40])[CH:35]=[CH:34][C:33]=2[S:32][C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2>CN(C)C=O>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:22][CH2:23][CH2:24][N:25]3[C:38]4[CH:37]=[C:36]([S:39][CH3:40])[CH:35]=[CH:34][C:33]=4[S:32][C:31]4[C:26]3=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:15][CH2:14]2)=[O:12])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 143914902-Methylthio-10-(3-chloropropyl)-phenothiazine

Product 1

HCID 143914914-(4-fluorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidineYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
78 °C

Procedure

To a stirred solution of sodium bicarbonate (10 g) in 40 ml of dimethylformamide was added 2.5 g of 4-(4-fluorobenzoyl)piperidine in 40 ml of dimethylformamide, and 4.5 g of 10-(3-chloropropyl)-2-methylthiophenothiazine in 20 ml of dimethylformamide. The reaction mixture was stirred at 78° C. for four hours, cooled, and filtered. The filtrate was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, filtred and concentrated to an oil. The oil was purified by high pressure liquid chromatography on a silica gel column, utilizing ethyl acetate as the eluent. Concentration of the appropriate fractions yielded 2.97 g (36%) of 4-(4-fluorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidine as an oil.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. additionThe filtrate was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by high pressure liquid chromatography on a silica gel column

Sources & evidence

ORD record
ord-f29eb838265d49318496d63d720be671
Source dataset
uspto-grants-1989_03
Patent number
US04812456

Reaction notes

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