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Dimethylformamide → 4-(2,4-dichlorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidine

HRID 1193986
Notes
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Reaction equation

HRID 1193986 reaction equation
CN(C)C=O.Cl[CH2:7][CH2:8][CH2:9][N:10]1[C:23]2[CH:22]=[C:21]([S:24][CH3:25])[CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2.[Cl:26][C:27]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:28]=1[C:29]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30].C(=O)(O)[O-].[Na+]>O>[Cl:26][C:27]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:28]=1[C:29]([CH:31]1[CH2:32][CH2:33][N:34]([CH2:7][CH2:8][CH2:9][N:10]2[C:23]3[CH:22]=[C:21]([S:24][CH3:25])[CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:35][CH2:36]1)=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 130763944-(2,4-Dichlorobenzoyl)piperidineHCID 143914902-Methylthio-10-(3-chloropropyl)-phenothiazine

Product 1

HCID 143914924-(2,4-dichlorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidineYield 79.9%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

To 75 ml of dry dimethylformamide was added 2.0 g of 10-(3-chloropropyl)-2-methylthiophenothiazine, 1.7 g of 4-(2,4-dichlorobenzoyl)piperidine, and 5.0 g of sodium bicarbonate. The reaction mixture was stirred at 90° for five hours, poured into 200 ml of water, and extracted with ethyl acetate. This extract was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil. This oil was purified by high pressure liquid chromatography on a silica gel column, utilizing ethyl acetate/dichloromethane (1:2 by volume) as the eluent. Concentration of the appropriate fractions yielded 2.7 g of 4-(2,4-dichlorobenzoyl)-1-[3-(2-methylthio-10H-phenothiazin-10-yl)propyl]piperidine as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThis extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis oil was purified by high pressure liquid chromatography on a silica gel column

Sources & evidence

ORD record
ord-c570386f11954147b7873fcfb4daa3df
Source dataset
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04812456

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes