Potassium Carbonate → 3-Methyl-6-phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

HRID 2163139Notes

Reaction equation

HRID 2163139 reaction equation
Br.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([OH:9])[CH:5](Br)[CH2:4]1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]([O:9]2)[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 227539263-Bromo-1-methyl-4-phenylpiperidin-4-ol--hydrogen bromide (1/1)

Product 1

HCID 4350913-Methyl-6-phenyl-7-oxa-3-azabicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-methyl-3-bromo-4-phenyl-4-piperidinol hydrobromide (4.10 g; 11.7 mmoles, described in Example 5) in water (5 ml) is cooled to 0°-5° C. Cold 10% aqueous sodium hydroxide solution (10 ml; 25 mmoles) is added dropwise with vigorous mechanical stirring, over a period of ten minutes. The solution is stirred for 30 min. and potassium carbonate is added to the solution at a temperature below 10° C. When the solution is saturated the solids are collected by filtration and crystallized from hexane at -70° C. to give the title compound, mp 44°-45° C. (R. E. Lyle and W. E. Krueger, supra, reported mp 43°-45° C.).

Workup

  1. filtrationare collected by filtration
  2. customcrystallized from hexane at -70° C.

Sources & evidence

ORD record
ord-dd6d31715fd24fa38ea4de6f2eadb784
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

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