Potassium Carbonate → HCID 86644720, compound

HRID 2407310Notes

Reaction equation

HRID 2407310 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@@:14]([CH2:19]OS(C)(=O)=O)([CH3:18])[CH2:13]1.[C:25]([OH:28])(=[S:27])[CH3:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@@:14]([CH2:19][S:27][C:25](=[O:28])[CH3:26])([CH3:18])[CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86644721HCID 86644721, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86644720HCID 86644720, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of methanesulfonic acid (S)-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-3-methylpiperidin-3-ylmethyl ester (927 mg, 2.61 mmol), thioacetic acid (373 μl, 399 mg, 5.24 mmol) and K2CO3 (721 mg, 5.22 mmol) in DMF (35 ml) was heated at 95° C. for 10 h. The mixture was evaporated to dryness, dissolved in DCM and washed two times with sat. aq NaHCO3. The organic phase was washed with brine, dried (Na2SO4) and evaporated to dryness to give 794 mg of the title compound.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in DCM
  3. washwashed two times with sat. aq NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9d362560b87c4ba6ae27028dcfce5df3
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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