Formaldehyde → 3-Methyl-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane--hydrogen chloride (1/1)

HRID 1903267Notes

Reaction equation

HRID 1903267 reaction equation
[ClH:1].[C:2]1([CH3:14])[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)=[CH:4][CH:3]=1.O.[OH-].[Na+].[CH2:18]=O>C(O)=O>[ClH:1].[CH3:18][N:10]1[CH2:11][CH:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:14])=[CH:7][CH:6]=3)([CH2:13]2)[CH2:9]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 479521-(4-Methylphenyl)-3-azabicyclo[3.1.0]hexane--hydrogen chloride (1/1)

Product 1

HCID 127198923-Methyl-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 4.19 g. of 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride and 20 ml. of water is made basic with sodium hydroxide. This mixture is extracted with ether and the ether is evaporated to give an oil. This oil is combined with 40 ml. of 97% formic acid and 35 ml. of 37% formaldehyde and the solution is heated on a steam bath for 2 hours. The solution is cooled, made basic with sodium hydroxide and extracted with ether. The extract is dried over magnesium sulfate, filtered, and the filtrate is saturated with hydrogen chloride. The precipitated crystals are collected and recrystallized from isopropyl alcohol to give 3-methyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride as colorless crystals, m.p. 197°-198° C.

Workup

  1. additionA mixture of 4.19 g
  2. extractionThis mixture is extracted with ether
  3. customthe ether is evaporated
  4. customto give an oil
  5. temperatureThe solution is cooled
  6. extractionextracted with ether
  7. dry with materialThe extract is dried over magnesium sulfate
  8. filtrationfiltered
  9. customThe precipitated crystals are collected
  10. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-7dcc74d5d3a141cdb5d1ac445e0084b8
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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