2,2,2-Trifluoroethanol → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-(2,2,2-trifluoroethoxymethyl)piperidine

HRID 2366005Notes

Reaction equation

HRID 2366005 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH2:19][O:20]S(C)(=O)=O)([CH3:18])[CH2:13]1.C([O-])([O-])=O.[K+].[K+].[CH2:31](O)[C:32]([F:35])([F:34])[F:33]>O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:18])([CH2:19][O:20][CH2:31][C:32]([F:35])([F:34])[F:33])[CH2:13]1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 86644718Methanesulfonic acid 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-ylmethyl ester

Product 1

HCID 251759661-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-(2,2,2-trifluoroethoxymethyl)piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methanesulfonic acid 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-ylmethyl ester (0.35 g, 0.98 mmol), K2CO3 (0.68 g) and trifluoroethanol (4 ml) was irradiated in a microwave reactor at 150° C. for 10 min. Water was added and the reaction mixture was extracted with DCM (2×20 ml). The combined organic phases were dried over Na2SO4, filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (DCM/MeOH, 90:10).

Workup

  1. customwas irradiated in a microwave reactor at 150° C. for 10 min
  2. extractionthe reaction mixture was extracted with DCM (2×20 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a0c941acc80b4844bd0ad0d1a8afe18f
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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