Ethyl chloroformate → HCID 57813476, compound

HRID 662083Notes

Reaction equation

HRID 662083 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].C(OC(Cl)=O)C.[NH:20]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1>C(Cl)Cl>[OH:26][CH:23]1[CH2:24][CH2:25][N:20]([C:8]([C:7]2[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=2)[C:3]([O:2][CH3:1])=[O:4])=[O:10])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 79341Piperidin-4-olHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 57813476HCID 57813476, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 3-[(methyloxy)carbonyl]benzoic acid (0.901 g, 5 mmol) in DCM (25 mL) was added TEA (0.697 mL, 5.00 mmol), EtOCOCl (0.480 mL, 5.0 mmol). This mixture was stirred at 0° C. for 10 mins and then 4-piperidinol (0.506 g, 5.00 mmol) was added. Stirring was continued at room temperature for 16 h. The reaction mixture was diluted with DCM (35 mL), washed with HOAc (20 mL, 10%), NaHCO3 (20 mL, 10%), water (20 mL), dried over Na2SO4, filtered and concentrated and purified by CombiFlash chomatograph to afford the title compound (0.696 g, 53%). LC-MS m/z 264 (M+H)+.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 16 h
  3. washwashed with HOAc (20 mL, 10%), NaHCO3 (20 mL, 10%), water (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by CombiFlash chomatograph

Sources & evidence

ORD record
ord-53850dc2b4a24b66b2f77a9c29f775ed
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

Loading…