1,4-Dioxane → 1-Methyl-4-phenyl-4-azido-3-hydroxypiperidine

HRID 2071765Notes

Reaction equation

HRID 2071765 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][N:6]1[CH2:11][CH2:10][C:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:12][CH:8]2[CH2:7]1.O1CCOCC1>O>[CH3:5][N:6]1[CH2:11][CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([N:1]=[N+:2]=[N-:3])[CH:8]([OH:12])[CH2:7]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 33557Sodium Azide2×HCID 4350913-Methyl-6-phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

Product 1

HCID 213272061-Methyl-4-phenyl-4-azido-3-hydroxypiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.4 G. of sodium azide (NaN3) in 6 ml. of water was added to a solution of 3.6 g. of 1-methyl-4-phenyl-3,4-epoxypiperidine in 20 ml. of dioxane and the resulting combined solution refluxed for 2 hours. A further portion of 1.4 g. of NaN3 in 6 ml. of water was then added and the reaction mixture refluxed overnight. Upon cooling 3.2 g. of crystals of the desired 1-methyl-4-phenyl-4-azido-3-hydroxypiperidine were obtained, which had a melting point of 170°-71° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturethe reaction mixture refluxed overnight
  3. temperatureUpon cooling 3.2 g

Sources & evidence

ORD record
ord-05b14f886f6943ceb506242964b9be9d
Source dataset
uspto-grants-1977_09
Patent number
US04048314

Reaction notes

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