Hydrogen Bromide → HCID 86734372, compound

HRID 1414534Notes

Reaction equation

HRID 1414534 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:22]C)[C:16]=3[S:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5][CH2:4]1)[CH3:2].Br.[OH-].[Na+]>C(O)(=O)C.O>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:22])[C:16]=3[S:15][C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 86734373HCID 86734373, compound

Product 1

HCID 86734372HCID 86734372, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1'-ethyl-4-methoxythioxanthene-9-spiro-4'-piperidine (1.625 g.) in glacial acetic acid (20 ml.) is added to 48% w/v hydrobromic acid (20 ml.) and refluxed with stirring for 5 hours. The mixture is cooled, diluted with water (500 ml.), cooled in ice and basified with 19N-sodium hydroxide solution and the solution washed with ether (× 3). The aqueous alkaline layer is acidfied to pH 1 with concentrated hydrochloric acid, neutralised with solid sodium bicarbonate and extracted with ethyl acetate (× 3). The combined ethyl acetate extracts are washed with water (× 3), dried over MgSO4 and the ethyl acetate removed by distillation in vacuo. The resulting sticky solid is triturated with ether to give 1'-ethyl-4-hydroxythioxanthene-9-spiro-4'-piperidine, m.p. 223°-225° C. on recrystallisation from dimethyl formamide/methanol/water.

Workup

  1. temperaturerefluxed
  2. temperatureThe mixture is cooled
  3. temperaturecooled in ice
  4. washthe solution washed with ether (× 3)
  5. extractionextracted with ethyl acetate (× 3)
  6. washThe combined ethyl acetate extracts are washed with water (× 3)
  7. dry with materialdried over MgSO4
  8. customthe ethyl acetate removed by distillation in vacuo
  9. customThe resulting sticky solid is triturated with ether

Sources & evidence

ORD record
ord-47cf9e4dd2a74f2eb603ea09283c5321
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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