Pyridine → Acetic acid 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-ylmethyl ester

HRID 2365992Notes

Reaction equation

HRID 2365992 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][OH:20])([CH3:18])[CH2:13]1.N1C=CC=CC=1.C(Cl)Cl.[C:30](OC(=O)C)(=[O:32])[CH3:31]>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]([CH2:19][O:20][C:30](=[O:32])[CH3:31])([CH3:18])[CH2:13]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 66726912[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol

Product 1

HCID 66727206Acetic acid 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of [1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol (0.5 g, 1.80 mmol), pyridine (0.29 ml) and DCM (40 ml) at 0° C. was added acetic anhydride (0.34 ml). The reaction mixture was stirred at RT for 6 h. Water was slowly added and the reaction mixture extracted with DCM (3×20 ml). The combined organic phases were dried over Na2SO4, filtered and the filtrate was evaporated to give the title compound.

Workup

  1. extractionthe reaction mixture extracted with DCM (3×20 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-33d5d591a58d42ca806726e559987cd1
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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