Sodium Hydroxide → Nisoxetine

HRID 1248851Notes

Reaction equation

HRID 1248851 reaction equation
C(O)(=O)C(O)=O.[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12807462HCID 12807462, compound

Product 1

HCID 4500Nisoxetine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-methyl 3-(o-methoxyphenoxy)-3-phenylpropylamine oxalate was dissolved in a minimum quantity of water with heating, and concentrated aqueous sodium hydroxide added. After cooling, the alkaline solution was extracted several times with ether. The combined ether extracts were washed with water and dried, and the ether removed therefrom in vacuo. N-methyl 3(o-methoxyphenoxy)-3-phenylpropylamine free base thus isolated was dissolved in ether, and the ether solution saturated with dry gaseous hydrogen chloride. N-methyl 3(o-methoxyphenoxy)-3-phenylpropylamine hydrochloride thus formed was recrystallized from ethyl acetate containing a small amount of methanol. N-methyl 3-(o-methoxyphenoxy)-3-phenylpropylamine hydrochloride thus prepared and purified melted at 129°-131° C.

Workup

  1. temperaturewith heating
  2. temperatureAfter cooling
  3. extractionthe alkaline solution was extracted several times with ether
  4. washThe combined ether extracts were washed with water
  5. customdried
  6. customthe ether removed

Sources & evidence

ORD record
ord-7f9beabf50404e0eb331d283183f0eca
Source dataset
uspto-grants-1986_12
Patent number
US04626549

Reaction notes

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