Triethylamine → HCID 12985692, compound

HRID 2184221Notes

Reaction equation

HRID 2184221 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:31](Cl)([CH3:34])(=[O:33])=[O:32]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][S:31]([CH3:34])(=[O:33])=[O:32])[CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10381067HCID 10381067, compound

Product 1

HCID 12985692HCID 12985692, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
66 °C

Procedure

To a mixture of 4.75 g (0.015 mol) of 1-(1-benzyl-4-piperidylacetyl)-4-hydroxypiperidine [1], 51 g of toluene, 1.68 g (0.017 mol) of triethylamine, 1.87 g (0.016 mol) of mesyl chloride was added dropwise at a temperature in the range of 0 to 10° C. and the reaction was allowed to proceed for 2 hours at the temperature in the range. Thereafter, the reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate and an aqueous solution of sodium chloride. The resultant organic layer was dried with anhydrous magnesium sulfate and concentrated under a reduced pressure. To the concentrated residue, 7 g of 2-propanol and 43 g of diisopropyl ether were added and the temperature of the mixture was increased. The mixture was stirred for 0.3 hours at a reflux temperature of 66° C. Thereafter the mixture was cooled to room temperature and subjected to filtration. The resultant wet crystal was dried under a reduced pressure, whereby 5.01 g of the title compound in the state of white powder was obtained (the yield was 84.7%).

Workup

  1. additionwas added dropwise at a temperature in the range of 0 to 10° C.
  2. washThereafter, the reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate
  3. dry with materialThe resultant organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. additionTo the concentrated residue, 7 g of 2-propanol and 43 g of diisopropyl ether were added
  6. temperaturethe temperature of the mixture was increased
  7. temperatureThereafter the mixture was cooled to room temperature
  8. filtrationsubjected to filtration
  9. dry with materialThe resultant wet crystal was dried under a reduced pressure, whereby 5.01 g of the title compound in the state of white powder
  10. customwas obtained (the yield was 84.7%)

Sources & evidence

ORD record
ord-74165972a08c4f319d9c55a453758981
Source dataset
uspto-grants-2005_05
Patent number
US06900326B2

Reaction notes

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