Sodium Hydroxide → HCID 131710588, compound

HRID 1414536Notes

Reaction equation

HRID 1414536 reaction equation
[ClH:1].[CH:2]1([CH2:6][N:7]2[CH2:12][CH2:11][C:10]3([C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([O:26]C)[C:20]=4[S:19][C:18]4[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3]1.[Al].C(Cl)(Cl)(Cl)[Cl:30].C(=O)=O.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH2:26].[ClH:30].[CH:2]1([CH2:6][N:7]2[CH2:12][CH2:11][C:10]3([C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=4[S:19][C:18]4[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:9][CH2:8]2)[CH2:3][CH2:4][CH2:5]1.[CH:2]1([CH2:6][N:7]2[CH2:12][CH2:11][C:10]3([C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=4[S:19][C:18]4[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:9][CH2:8]2)[CH2:3][CH2:4][CH2:5]1.[ClH:1]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 5359268AluminumHCID 86602444Carbontetrachloride dry-iceHCID 131710590HCID 131710590, compound

Product 1

HCID 131710588HCID 131710588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1'-cyclobutylmethyl-4-methoxythioxanthene-9-spiro-4'-piperidine hydrochloride (600 mg.) in dry methylene chloride (12 ml.) in an atmosphere of nitrogen, protected from light using aluminium foil and at -10° C. (carbontetrachloride/dry-ice bath), is treated with boron tribromide (0.6 ml.) in one portion. The reaction temperature is allowed to rise to ambient temperature and stirring is continued for 1.5 hours. The suspension is cooled in ice, treated dropwise with 2N--NaOH solution until solution is complete. The methylene chloride is distilled off in vacuo and the solution neutralised with glacial acetic acid. The pink solid is filtered off, washed with water and dried in vacuo over phosphorous pentoxide at 60° C. The solid is suspended in hot ethanol, and treated with ethereal hydrochloric acid, causing the solid to dissolve. The hydrochloride crystallises almost immediately to give 1'-cyclobutylmethyl-4-hydroxythioxanthene-9-spiro-4'-piperidine hydrochloride hemihydrate, m.p. 270° C. (decomposition).

Workup

  1. customto rise to ambient temperature
  2. temperatureThe suspension is cooled in ice
  3. additiontreated dropwise with 2N
  4. distillationThe methylene chloride is distilled off in vacuo
  5. filtrationThe pink solid is filtered off
  6. washwashed with water
  7. dry with materialdried in vacuo over phosphorous pentoxide at 60° C
  8. additiontreated with ethereal hydrochloric acid
  9. dissolutionto dissolve
  10. customThe hydrochloride crystallises almost immediately

Sources & evidence

ORD record
ord-92581be82cef4a329e408c5b7ee65970
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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