Ethyl chloroformate → 1-Ethoxycarbonyl-4-((benzothiazol-2-yl)methyl)piperidine

HRID 1386783Notes

Reaction equation

HRID 1386783 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C1COCC1>[CH2:28]([O:27][C:25]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:26])[CH3:29]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 211807101-Benzyl-4-((benzothiazol-2-yl)methyl)piperidine

Product 1

HCID 211807791-Ethoxycarbonyl-4-((benzothiazol-2-yl)methyl)piperidineYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 500 mg of 1-benzyl-4-((benzothiazol-2-yl)methyl)piperidine (from EXAMPLE 163, Step D) in 10 mL of THF was added 185 mg of ethyl chloroformate at rt. The reaction was stirred at rt for 5 h. The reaction mixture was partitioned between H2O and EtOAc. The aqueous phase was extracted with EtOAc (3×). The combined organic phases were washed with sat'd NaCl and dried over MgSO4. Concentration afforded 320 mg of the title compound as a oil.

Workup

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

Sources & evidence

ORD record
ord-d1675590bc0d469b85cf20ad9de1a05f
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

Loading…