Dimethylamine → HCID 19835496, compound

HRID 477385Notes

Reaction equation

HRID 477385 reaction equation
C([NH:4][C:5]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]1[O:11][CH2:10]1)(=O)C.[CH3:19][NH:20][CH3:21].O>C(O)(=O)C>[NH2:4][C:5]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]([OH:11])[CH2:10][N:20]([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 19835525HCID 19835525, compound

Product 1

HCID 19835496HCID 19835496, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.085 mol (21.5 g) of 1-(2'-acetylamino-4'-nitrophenoxy)-2,3-epoxypropane (compound described in Example (4) is introduced into 100 ml of a 40% strength aqueous solution of dimethylamine, and the reaction mixture is stirred for 30 minutes at ambient temperature. After dilution by the addition of 225 ml of iced water, followed by neutralisation with acetic acid, the mixture is evaporated to dryness in vacuo. The dried residue is taken up in 150 ml of ethyl acetate. After washing with acetone, the material which is insoluble in ethyl acetate consists of 28.5 g of 1-(2'-acetylamino-4'-nitrophenoxy)-3-dimethylaminopropan-2-ol. This acetylated derivative is heated under reflux for two hours in 220 ml of ethanol saturated with hydrogen chloride. After the reaction medium has cooled, the expected product in the form of the hydrochloride is filtered off. After this hydrochloride has been dissolved in water and the aqueous solution has been rendered alkaline with sodium hydroxide solution, the 1-(2'-amino-4' -nitrophenoxy)-3-dimethylaminopropan-2-ol is precipitated in the form of crystals.

Workup

  1. customthe mixture is evaporated to dryness in vacuo
  2. washAfter washing with acetone
  3. temperatureThis acetylated derivative is heated
  4. temperatureunder reflux for two hours in 220 ml of ethanol saturated with hydrogen chloride
  5. temperatureAfter the reaction medium has cooled
  6. filtrationthe expected product in the form of the hydrochloride is filtered off
  7. dissolutionAfter this hydrochloride has been dissolved in water
  8. customthe 1-(2'-amino-4' -nitrophenoxy)-3-dimethylaminopropan-2-ol is precipitated in the form of crystals

Sources & evidence

ORD record
ord-711ab535226d4affb3a5d45b094c28e9
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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