Sodium Hydroxide → Nisoxetine

HRID 1446930Notes

Reaction equation

HRID 1446930 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-phenyl-propylamine 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-d6db5a48ad404ad285c70c42b37c23af
Source dataset
uspto-grants-1982_02
Patent number
US04314081

Reaction notes

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