1-Ethoxycarbonyl-4-((benzothiazol-2-yl)methyl)piperidine → 2-(Piperidin-4-ylmethyl)benzo[d]thiazole

HRID 1386784Notes

Reaction equation

HRID 1386784 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:8][CH2:7]1)=O)C>CCO.[OH-].[K+]>[S:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[CH2:12][CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 211807791-Ethoxycarbonyl-4-((benzothiazol-2-yl)methyl)piperidine

Product 1

HCID 172214952-(Piperidin-4-ylmethyl)benzo[d]thiazoleYield 78.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 300 mg of 1-ethoxycarbonyl-4-((benzothiazol-2-yl)methyl)piperidine (from EXAMPLE 163, Step E) in 5 mL of EtOH and 5 mL of KOH (50 wt. % solution) was refluxed for 18 h. The reaction mixture was partitioned between H2O and EtOAc. Aqueous phase was extracted with EtOAc (3×). The combined organic phases were washed with sat'd NaCl and dried over anhydrous MgSO4. Concentration afforded 180 mg of the title compound as a brown solid.

Workup

  1. customThe reaction mixture was partitioned between H2O and EtOAc
  2. extractionAqueous phase was extracted with EtOAc (3×)
  3. washThe combined organic phases were washed with sat'd NaCl
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-0b4fa9a6d8474ddfb4d07c23a056446a
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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