Dodecanoyl chloride → 2,6-Diphenyl-4-piperidyl laurate

HRID 1646778Notes

Reaction equation

HRID 1646778 reaction equation
[C:1]1([CH:7]2[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:25](Cl)(=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>O1CCCC1.[Cl-].[Na+].O>[C:25]([O:13][CH:11]1[CH2:12][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:8][CH:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10]1)(=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 130689322,6-Diphenylpiperidin-4-olHCID 178418339Butyllithium

Product 1

HCID 152504842,6-Diphenyl-4-piperidyl laurateYield 74.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-20 °C

Procedure

To a -70° C. solution of 2.50 g (9.9 mmol) of 2,6-diphenyl-4-hydroxypiperidine in 80 ml of dry tetrahydrofuran (THF), 4.2 mL (10.5 mmol) of n-butyllithium (2.5M in hexanes) is added dropwise. The mixture is warmed to -20° C. and stirred for 30 minutes. The solution is then cooled again to -70° C. and a solution of 2.2 g (9.9 mmol) of lauroyl chloride in 20 mL of dry THF is then added dropwise. The mixture is warmed to room temperature and stirred for 18 hours. The mixture is added to 250 mL of brine and then extracted with 2×200 mL of ether. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by liquid chromatography (LC) (silica gel, ethyl acetate/hexane) to give 3.2 g (74%) of the title compound as a white solid: mp 40°-42° C.

Workup

  1. temperatureThe solution is then cooled again to -70° C.
  2. temperatureThe mixture is warmed to room temperature
  3. stirringstirred for 18 hours
  4. extractionextracted with 2×200 mL of ether
  5. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by liquid chromatography (LC) (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-43cf686886744bf58f632714cc6c2620
Source dataset
uspto-grants-1993_01
Patent number
US05180829

Reaction notes

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