Phosphorus oxychloride → 3-Chloromethyl-1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine

HRID 2365988Notes

Reaction equation

HRID 2365988 reaction equation
P(Cl)(Cl)([Cl:3])=O.[O:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]1[CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][C:19]([CH2:24]O)([CH3:23])[CH2:18]1>>[Cl:3][CH2:24][C:19]1([CH3:23])[CH2:20][CH2:21][CH2:22][N:17]([CH2:16][CH:7]2[O:6][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH2:18]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66726912[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol

Product 1

HCID 251756633-Chloromethyl-1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine

Procedure

A mixture of phosphorus oxychloride (1.93 ml, 0.02 mmol) and [1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol (0.2 g, 0.72 mmol) was refluxed for 3 h. Excess of phosphorus oxychloride was evaporated. Water was slowly added and the reaction mixture was made alkaline with aq NaOH and extracted with DCM (3×5 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. temperaturewas refluxed for 3 h
  2. customExcess of phosphorus oxychloride was evaporated
  3. additionWater was slowly added
  4. extractionextracted with DCM (3×5 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-42783e20557c4b4d84009b638235afd9
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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