Pyridine → HCID 14835767, compound

HRID 1709259Notes

Reaction equation

HRID 1709259 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH2:12]O)=[CH:6][CH:5]=1)=[O:3].N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O.O.[N:33]1([CH:39]2[C:49]3[C:44](=[N:45][CH:46]=[CH:47][CH:48]=3)[CH2:43][CH2:42][C:41]3[CH:50]=[CH:51][CH:52]=[CH:53][C:40]2=3)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH2:12][N:36]2[CH2:37][CH2:38][N:33]([CH:39]3[C:49]4[C:44](=[N:45][CH:46]=[CH:47][CH:48]=4)[CH2:43][CH2:42][C:41]4[CH:50]=[CH:51][CH:52]=[CH:53][C:40]3=4)[CH2:34][CH2:35]2)=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 14835705HCID 14835705, compoundHCID 23037272HCID 23037272, compound

Product 1

HCID 14835767HCID 14835767, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1.96 g of (E)-3-(4-methylsulfinylphenyl)allyl alcohol was dissolved in 40 ml of methylene chloride. To the solution were added 1.34 g of 4-N,N-dimethylamino)pyridine and 2.19 g of p-toluenesulfonyl chloride with ice-cooling. The mixture was stirred for 4 hours at room temperature. To the reaction mixture were added 1.32 g of triethylamine and 3.15 g of 5-(piperazin- 1-yl)-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridine dihydrate. The mixture was stirred for 5 hours at room temperature. The reaction mixture was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: chloroform/methanol=35/1) to obtain 2.31 g of 5-[4-{(E)-3-(4-methylsulfinylphenyl)allyl}piperazin-1-yl]-10,11-dihydro-5H-benzo-[4,5]cyclohepta[1,2-b]pyridine. It was recrystallized from isopropyl alcohol to obtain 1.85 g of colorless crystals having a melting point of 166°-168° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 5 hours at room temperature
  3. washThe reaction mixture was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by a column chromatography (eluant: chloroform/methanol=35/1)

Sources & evidence

ORD record
ord-5daa30582ede47a88491e30dcf3472d0
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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