Ethanol → HCID 13371771, compound

HRID 1388547Notes

Reaction equation

HRID 1388547 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[S:8](=[O:17])(=[O:16])[CH2:7][C:6]=2[CH:18]=1.[H-].[Na+].[N:21]1([CH2:27][CH2:28][CH2:29]Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[S:8](=[O:16])(=[O:17])[CH:7]([CH2:29][CH2:28][CH2:27][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:6]=2[CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 12930973HCID 12930973, compound

Product 1

HCID 13371771HCID 13371771, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4.18 g 2-chloro-11H-dibenz (b,f)-1,4-oxathiepin 10,10-dioxide in 40 ml of dimethylformamide was treated with 0.65 g of sodium hydride and the mixture stirred for 4.5 hours at 70° C. Thereafter, 10 ml of 3-piperidinopropyl chloride were added and the mixture stirred for 3.5 hours at 70° C. It was then decomposed by dropwise addition of 4 ml of ethanol and diluted with 700 ml of water and extracted with benzene. From the benzene solution the base was extracted with 100 ml of 3M-HCl. The separated acid aqueous solution was made alkaline with aqueous ammonia and the base extracted with chloroform. The extract was dried with potassium carbonate and evaporated. The residue was chromatographed on a column of 400 g of neutral aluminum oxide (activity II). The less polar impurities were eluted with benzene and 4.37 g of homogeneous oily base were eluted with benzene and 4.37 g of homogeneous oily base were eluted with chloroform. Neutralization with hydrogen chloride in a mixture of ethanol and ether yielded the hydrochloride. By crystallization from a mixture of ethanol and ether the pure product was obtained, m.p. 177°-179° C.

Workup

  1. stirringthe mixture stirred for 3.5 hours at 70° C
  2. extractionextracted with benzene
  3. extractionFrom the benzene solution the base was extracted with 100 ml of 3M-HCl
  4. extractionthe base extracted with chloroform
  5. dry with materialThe extract was dried with potassium carbonate
  6. customevaporated
  7. customThe residue was chromatographed on a column of 400 g of neutral aluminum oxide (activity II)
  8. washThe less polar impurities were eluted with benzene and 4.37 g of homogeneous oily base
  9. washwere eluted with benzene and 4.37 g of homogeneous oily base
  10. washwere eluted with chloroform
  11. additionNeutralization with hydrogen chloride in a mixture of ethanol and ether

Sources & evidence

ORD record
ord-c7563449d5d8488db07185b527312123
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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