Dimethylamine → 1-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

HRID 229322

Reaktionsgleichung

Reaktionsgleichung von HRID 229322
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>CO.CN(C)C=O>[CH3:15][N:16]([CH3:17])[CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 674DimethylamineHCID 213272-((4-Nitrophenoxy)methyl)oxirane

Produkt 1

HCID 31320441-(Dimethylamino)-3-(4-nitrophenoxy)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-nitrophenoxymethyl)-oxirane (0.1 mol, 19.52 g) in methanol (150 mL) and dimethyl formamide (50 mL) was added a 2 M solution of dimethylamine in methanol (0.2 mol, 100 mL), and the mixture was stirred at rt overnight. The solvent was evaporated, and the residue was dissolved in a mixture of methylene chloride (300 mL) and methanol (30 mL). A portion of 1 N HCl in diethyl ether (150 mL) was added dropwise, and an oil formed. The oil was separated (ethereal layer was decanted), and the oil was dried under vacuum, yielding 1-dimethylamino-3-(4-nitro-phenoxy)-propan-2-ol (16.6 g) as its hydrochloride salt. MS (ES+) m/z: 240.9 (M+H+). The compound was used as such for the next reaction.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in a mixture of methylene chloride (300 mL) and methanol (30 mL)
  3. additionA portion of 1 N HCl in diethyl ether (150 mL) was added dropwise
  4. customan oil formed
  5. customThe oil was separated
  6. custom(ethereal layer was decanted)
  7. customthe oil was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0e4c415c1b414c53872ae1fd550760bd
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563781B2

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