Hydrochloric Acid → HCID 13151512, compound

HRID 1648872Notes

Reaction equation

HRID 1648872 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[NH2:27])[CH2:16][CH2:15]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:28](=S)=[S:29].[OH-].[K+].[ClH:33]>O.C(O)C>[ClH:33].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH:11]([CH2:13][N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[NH:27][C:28]4=[S:29])[CH2:18][CH2:19]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 20481051HCID 20481051, compound

Product 1

HCID 13151512HCID 13151512, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 13.7 g of 1-[2-(4-fluorophenyl)-tetrahydro-4-furylmethyl]-4-(2-aminoanilino)piperidine, 18 g of carbon disulfide and 4.2 g of potassium hydroxide is heated under reflux with stirring for 3.5 hours and then cooled. To the mixture are added 200 ml of ethanol, 126 ml of water and 32 ml of concentrated hydrochloric acid, and the whole is heated under reflux for 20 minutes. The solvent is then distilled off under reduced pressure. The residue is made alkaline with aqueous ammonia and extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluant. To the thus obtained oil is added ethanolic hydrochloric acid. The crystals precipitated are collected by filtration and recrystallized from methanol-isopropyl ether to give 1-[1-(2-(4-fluorophenyl)-tetrahydro-4-furylmethyl)-4-piperidyl]benzimidazoline-2-thione hydrochloride as colorless needles, melting at 269°-270° C. with decomposition.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. temperaturethe whole is heated
  5. temperatureunder reflux for 20 minutes
  6. distillationThe solvent is then distilled off under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe extract is washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel with chloroform eluant
  12. additionTo the thus obtained oil is added ethanolic hydrochloric acid
  13. customThe crystals precipitated
  14. filtrationare collected by filtration
  15. customrecrystallized from methanol-isopropyl ether

Sources & evidence

ORD record
ord-162f8c014bbb456aa7ebfd0365fbdbf9
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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