Ethanol → HCID 23033856, compound

HRID 1393350Notes

Reaction equation

HRID 1393350 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)C>C(OCC)C>[N:14]1([C:2]2[S:3][C:4]3[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 230338792-Bromo-1,3-benzothiazole-7-carboxylic acid

Product 1

HCID 23033856HCID 23033856, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of ethyl ester of 2-bromobenzothiazole-7-carboxylic acid (572 mg, 2.00 mmol), piperidine (5 ml) and ethanol (1 ml) was stirred at 70-75° C. for 2.5 hrs. Diethyl ether (15 ml) was added to the mixture at room temperature and the precipitates were filtered off and washed with diethyl ether. The filtrate and washings were combined and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to give ethyl ester of 2-piperidinobenzothiazole-7-carboxylic acid (526 mg, 90%) as pale orange crystals.

Workup

  1. filtrationthe precipitates were filtered off
  2. washwashed with diethyl ether
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-81da932fa6cc48f284da6c53c1200355
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…