Ethyl chloroformate → HCID 57813476, compound

HRID 564559Notes

Reaction equation

HRID 564559 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), and EtOCOCl (0.480 mL, 5.0 mmol), stirred at 0° C. for 10 min. and then 4-piperidinol (0.506 g, 5.00 mmol) was added. This mixture was then stirred 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 chromatograph to afford the title compound (0.696 g, 53%). LC-MS m/z 264 (M+H)+.

Workup

  1. stirringThis mixture was then stirred at room temperature for 16 h
  2. washwashed with HOAc (20 mL, 10%), NaHCO3 (20 mL, 10%), water (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-37d798188a3a4d24829910c673865167
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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