Bromine → HCID 68491393, compound

HRID 389016Notes

Reaction equation

HRID 389016 reaction equation
[Br:1]Br.[S:3]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:6]=2[CH:5]=[CH:4]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:4]1[S:3][C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 27400PizotylineHCID 516892Sodium Bicarbonate

Product 1

HCID 68491393HCID 68491393, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (1.0 mL, 19.5 mmol) was added dropwise to a chloroform (50 mL) solution of 4-(9,10-dihydro-1-thiabenzo[f]azulen-4-ylidene)-1-methylpiperidine (5.76 g, 19.5 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hours. Thereafter, a saturated aqueous sodium bicarbonate solution was added to the mixture, and an organic layer was separated. The organic layer was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the residue was purified by column chromatography (chloroform-methanol=9:1), to give 5.6 g (91%) of the captioned compound in the form of white crystals.

Workup

  1. customan organic layer was separated
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvents were distilled off under a reduced pressure
  5. customthe residue was purified by column chromatography (chloroform-methanol=9:1)

Sources & evidence

ORD record
ord-b482172c4c4c4300aa98e78639a83e78
Source dataset
uspto-grants-2013_02
Patent number
US08377967B2

Reaction notes

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