Pyridinium chloride → HCID 22139451, compound

HRID 1825800Notes

Reaction equation

HRID 1825800 reaction equation
C[O:2][C:3]1[C:8]2[S:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>O>[CH:6]1[C:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9][C:8]=2[C:3]([OH:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22139417HCID 22139417, compound

Product 1

HCID 22139451HCID 22139451, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

4-Methoxy-10,11-dihydro-dibenzo[b,f]thiepine (2.42 g, 10 mmol) and pyridine hydrochloride (15 g) were heated with stirring at 180° C. for one hour. Water (100 ml) was added to the reaction mixture and the organics were extracted with ethyl acetate (3×100 ml). The organics were combined and washed with 2N HCl (50 ml), brine (50 ml), and dried over magnesium sulphate. The solvent were removed in vacuo and the residue was purified by column chromatography (1:9; dichloromethane:hexane) to give the desired compound as a white solid (1.55 g, 68%). 1HNMR (300 MHz, DMSO-d6): δH=3.13–3.23 (4H, m), 6.70 (2H, t), 6.97–7.15 (4H, m), 7.38 (1H,s) 9.78 (1H, s); m/z (LC-MS, ESP), RT=4.59 min, (M++1)=229.

Workup

  1. extractionthe organics were extracted with ethyl acetate (3×100 ml)
  2. washwashed with 2N HCl (50 ml), brine (50 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent were removed in vacuo
  5. customthe residue was purified by column chromatography (1:9; dichloromethane:hexane)

Sources & evidence

ORD record
ord-69c3e84f6c104fa783e14d72139d202d
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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