Potassium Carbonate → HCID 66615618, compound

HRID 1878792Notes

Reaction equation

HRID 1878792 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][N:10]2[CH2:11][CH2:12][CH:7]([O:6][C:5]3[CH:13]=[CH:14][C:15]([Cl:16])=[C:3]([Cl:2])[C:4]=3[CH3:17])[CH2:8][CH2:9]2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineHCID 66615669HCID 66615669, compound

Product 1

HCID 66615618HCID 66615618, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
20 °C

Procedure

Acetonitrile (144 mL) and water (336 mL) were added to a mixture of 4-(3,4-dichloro-2-methyl-phenoxy)-piperidine hydrochloride (60 g), 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (74.7 g) and potassium carbonate (57.3 g) and the mixture was heated to reflux for 7 h, then cooled over 30 min to 75° C. and held at 75° C. for 14 h, then heated over 30 min to reflux. Acetonitrile (192 mL) was added and then the mixture was cooled to 20° C. over 2 h to give a suspension. The suspension was filtered under vacuum, the filter cake was washed with water (180 mL) and then with acetonitrile (180 mL) and dried under vacuum at 40° C. to give 4-[4-(3,4-dichloro-2-methyl-phenoxy)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (73.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 7 h
  3. temperaturecooled over 30 min to 75° C.
  4. temperatureheated over 30 min
  5. temperatureto reflux
  6. customto give a suspension
  7. filtrationThe suspension was filtered under vacuum
  8. washthe filter cake was washed with water (180 mL)
  9. dry with materialwith acetonitrile (180 mL) and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-9da2d3d6ddbf404eb0495e777a4e04c9
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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