Acetic Acid → 1′-Methylspiro[benzothiazole-2(3H),4′-piperidine]

HRID 2198870Notes

Reaction equation

HRID 2198870 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.C(O)(=O)C.C1(C)C=CC=CC=1>O>[CH3:9][N:10]1[CH2:15][CH2:14][C:13]2([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 87132-AminothiophenolHCID 740491-Methyl-4-piperidone

Product 1

HCID 28263101′-Methylspiro[benzothiazole-2(3H),4′-piperidine]

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 125.5 g 2-amino-thiophenol, 147 g N-methyl-4-piperidone, 2 ml acetic acid and 400 ml toluene is refluxed with a water separator for 2 hours. The mixture is evaporated in vacuo. The residue is recrystallised from methylene chloride/ether/petroleum ether to give the heading compound, m.p. 135°-140°.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customThe residue is recrystallised from methylene chloride/ether/petroleum ether
  3. customto give the heading compound, m.p. 135°-140°

Sources & evidence

ORD record
ord-b5f81450be074655967b563b4a334c20
Source dataset
uspto-grants-1982_11
Patent number
US04360525

Reaction notes

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