Benzyl chloroformate → HCID 21936871, compound

HRID 989888Notes

Reaction equation

HRID 989888 reaction equation
Cl.[CH:2]1([C:8]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCOCC1>[C:24]1([CH2:23][O:22][C:20]([N:11]2[CH2:10][CH2:9][C:8]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]2)=[O:21])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 6984437692329-61-8

Product 1

HCID 21936871HCID 21936871, compoundYield 74,286.398%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

A 2-L, three-necked, round-bottomed flask equipped with a mechanical stirrer and two addition funnels was charged with 4-cyclohexyl-4-piperidinecarboxylic acid hydrochloride (8-3) (157.9 g, 0.637 mol), 1 L of dioxane, and 255 mL of 5 N NaOH solution. The mixture was cooled at about 5° C., and then benzyl chloroformate (92 mL, 0.643 mmol) and 127 mL of 5 N NaOH solution were added dropwise simultaneously via two separate addition funnels while maintaining the temperature at or below 10° C. The reaction was monitored by TLC and, upon completion, the resulting mixture was diluted with 1 L of water and concentrated. The residue was diluted with 2 L of water and the pH was adjusted to about 12 using 5 N NaOH solution. The mixture was then extracted with 1 L of ethyl acetate. The aqueous layer was acidified to pH 1.5-2.0 using 2 N HCl solution, and extracted with three 1-L portions of ethyl acetate. The combined organic layers were washed with 1 L of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to give 165 g of title compound 8-4 as a white solid.

Workup

  1. additiontwo addition funnels
  2. customseparate
  3. additionaddition funnels
  4. temperaturewhile maintaining the temperature at or below 10° C
  5. additionthe resulting mixture was diluted with 1 L of water
  6. concentrationconcentrated
  7. additionThe residue was diluted with 2 L of water
  8. extractionThe mixture was then extracted with 1 L of ethyl acetate
  9. extractionextracted with three 1-L portions of ethyl acetate
  10. washThe combined organic layers were washed with 1 L of saturated sodium chloride solution
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-a5b3c98d4f19401ebaab6113c2f0ca1e
Source dataset
uspto-grants-2002_10
Patent number
US06458790B2

Reaction notes

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