Water → HCID 20344064, compound

HRID 2049692Notes

Reaction equation

HRID 2049692 reaction equation
S(Cl)(Cl)=O.[C:5]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([C:14]([OH:16])=O)[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl.C(Cl)(Cl)Cl>[C:5]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[C:14]2=[O:16])[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 20343984HCID 20343984, compound

Product 1

HCID 20344064HCID 20344064, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.13 ml of freshly distilled thionyl chloride are added to a mixture of 0.3 g of 1-acetyl-4-[2-(4-fluorophenylthio)phenyl]piperidine-4-carboxylic acid in 3 ml of methylene chloride. The mixture is stirred for 155 minutes before being diluted with 7.5 ml of methylene chloride. The reaction solution is added dropwise to 0.17 g of aluminum chloride. Thereafter, the reaction is stirred for 15 minutes and then refluxed for three hours. The refluxed mixture is stirred for 72 hours before the sequential addition of ice, 25 ml of water and 25 ml of chloroform. The mixture is shaken and then the layers separate. The aqueous layer is extracted twice with 25 ml portions of chloroform and the combined chloroform solutions are successively washed with one 20 ml portion of a 10% sodium hydroxide solution, two 30 ml portions of water and 1 ml of saturated sodium chloride solution, dried and evaporated. The residue is chromatographed on 20×20 cm. preparative, thick layer, silica gel plates with an acetone-ether-methylene chloride (1:1:1) mixture. The purified product is dissolved in benzene and diluted with hexane and then the solvent is removed, providing 1'-acetyl-2-fluoro-10,11-dihydro-11-oxospiro[dibenz(b,f)thiepin-10,4'-piperidine].

Workup

  1. stirringThereafter, the reaction is stirred for 15 minutes
  2. temperaturerefluxed for three hours
  3. stirringThe mixture is shaken
  4. customthe layers separate
  5. extractionThe aqueous layer is extracted twice with 25 ml portions of chloroform
  6. washthe combined chloroform solutions are successively washed with one 20 ml portion of a 10% sodium hydroxide solution, two 30 ml portions of water and 1 ml of saturated sodium chloride solution
  7. customdried
  8. customevaporated
  9. customThe residue is chromatographed on 20×20 cm
  10. dissolutionThe purified product is dissolved in benzene
  11. additiondiluted with hexane
  12. customthe solvent is removed

Sources & evidence

ORD record
ord-f1a355246e28461e93fe76fbe94f3cab
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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