3-Acetyl-1-(p-aminophenyl)-3-azabicyclo[3.1.0]hexane → 3-Acetyl-1-(p-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane

HRID 371949Notes

Reaction equation

HRID 371949 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:10]3[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=3)([CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2].N([O-])=[O:18].[Na+]>Cl>[C:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([OH:18])=[CH:12][CH:11]=3)([CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 204683323-Acetyl-1-(p-aminophenyl)-3-azabicyclo[3.1.0]hexaneHCID 23668193Sodium Nitrite

Product 1

HCID 203522433-Acetyl-1-(p-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-acetyl-1-(p-aminophenyl)-3-azabicyclo[3.1.0]hexane in 8N hydrochloric acid is diazotized at 0° C, with aqueous sodium nitrite. The solution is then allowed to stand at ambient temperature until the evolution of nitrogen ceases. This mixture is then extracted with ether, and the extract is dried over sodium sulfate, filtered and then evaporated under reduced pressure to give 3-acetyl-1-(p-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane.

Workup

  1. customto stand at ambient temperature until the evolution of nitrogen ceases
  2. extractionThis mixture is then extracted with ether
  3. dry with materialthe extract is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-70693089ac8046d4a43e434b407e55c4
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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