Hydrochloric Acid → 3-Ethyl-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane--hydrogen chloride (1/1)

HRID 1903275Notes

Reaction equation

HRID 1903275 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)=[CH:3][CH:2]=1.[CH2:14](I)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].[ClH:23]>CCOCC.C1(C)C=CC=CC=1>[ClH:23].[CH2:14]([N:9]1[CH2:10][CH:11]2[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=3)([CH2:12]2)[CH2:8]1)[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 47953Bicifadine

Product 1

HCID 160477373-Ethyl-1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.4 g. of 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane (Example 32), 7.3 g. of ethyl iodide and 8.9 g. of sodium carbonate in 60 ml. of toluene is heated at reflux for 18 hrs. Filtration and evaporation of this mixture gives a residue which is dissolved in ether. Addition of ethanolic hydrogen chloride gives a precipitate which is recrystallized from acetonitrile to give the desired product as colorless crystals, m.p. 175°-176° C.

Workup

  1. additionA mixture of 7.4 g
  2. temperatureat reflux for 18 hrs
  3. filtrationFiltration and evaporation of this mixture
  4. customgives a residue which
  5. customgives a precipitate which
  6. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8536fa9b8caa4af6b5beeb3361183309
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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