Methyl p-toluenesulfonate → N-(2,3-dimethylbenzothiazole-6-sulfonyl)piperidine tosylate

HRID 84776

Reaction equation

HRID 84776 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:20][O:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>>[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)([OH:24])(=[O:23])=[O:21].[CH3:1][CH:2]1[N:6]([CH3:20])[C:5]2[CH:7]=[CH:8][C:9]([S:11]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)(=[O:12])=[O:13])=[CH:10][C:4]=2[S:3]1

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 10756752-Methyl-6-(piperidine-1-sulfonyl)-benzothiazole

Product 1

HCID 86609325N-(2,3-dimethylbenzothiazole-6-sulfonyl)piperidine tosylateYield 86%

Conditions

Temperature
130 °C

Procedure

A mixture of Compound 3 (1.0 g, 3.4 mmol) and p-toluenesulfonic acid methyl ester (0.94 g, 5.1 mmol) was heated in a pressure tube at 130° C. for 1 hour. The mixture was allowed to cool to room temperature, and the resulting mass was triturated with acetone (25 ml) until a gray colored solid separated. The solid was collected by centrifugation, washed with acetone and dried under vacuum to yield 1.4 g (86%) of Compound 4 whose structure is given below:

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting mass was triturated with acetone (25 ml) until a gray colored solid
  3. customseparated
  4. customThe solid was collected by centrifugation
  5. washwashed with acetone
  6. customdried under vacuum

Sources & evidence

ORD record
ord-799a2ead17e84cfe838192fd9b6aae4c
Source dataset
uspto-grants-2014_09
Patent number
US08846952B2

Linked notes

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