Potassium Carbonate → 2-Bromo-10-[3-(4-p-fluorobenzoylpiperidinyl)propyl]phenothiazine hydrochloride

HRID 2397445Notes

Reaction equation

HRID 2397445 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][Cl:19])[C:4]=2[CH:3]=1.[F:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:19].[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][CH2:18][N:30]3[CH2:31][CH2:32][CH:27]([C:25](=[O:26])[C:24]4[CH:23]=[CH:22][C:21]([F:20])=[CH:34][CH:33]=4)[CH2:28][CH2:29]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 21438254HCID 21438254, compound

Product 1

HCID 214382682-Bromo-10-[3-(4-p-fluorobenzoylpiperidinyl)propyl]phenothiazine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 8.86 g. (0.025 mole) of 2-bromo-10-(3-chloropropyl)phenothiazine, 5.18 g. (0.025 mole) of 4-(p-fluorobenzoyl)piperidine and 10 g. of potassium carbonate in 100 ml. of dry dimethylformamide was heated at 90°-100° C. for 24 hours. The cooled reaction mixture was filtered, the dimethylformamide removed at reduced pressure and the residue mixed with dry ether and the ether mixture filtered to remove solids. The dry ether solution was treated with ethereal hydrogen chloride to give the 2-bromo-10-[3-(4-p-fluorobenzoylpiperidinyl)propyl]phenothiazine hydrochloride.

Workup

  1. additionA stirred mixture of 8.86 g
  2. customThe cooled reaction mixture
  3. filtrationwas filtered
  4. customthe dimethylformamide removed at reduced pressure
  5. additionthe residue mixed with dry ether
  6. filtrationthe ether mixture filtered
  7. customto remove solids
  8. additionThe dry ether solution was treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-34a347a30a2044a8bf979f463c7fc283
Source dataset
uspto-grants-1977_05
Patent number
US04021552

Reaction notes

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