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

HRID 433922

Reaktionsgleichung

Reaktionsgleichung von HRID 433922
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[CH3:15][N:16]([CH2:11][CH:10]([OH:12])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:17]

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 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(4-Nitrophenoxy)-2,3-epoxypropane (Reference Example 1-B, 4.3 g) was dissolved in methanol (30 ml) and DMF (10 ml). Dimethylamine (2M solution in methanol, 17 ml) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was evaporated to dryness and the residue was dissolved in saturated sodium bicarbonate solution and ethyl acetate. The ethyl acetate layer was separated and washed twice with saturated brine, dried over anhydrous sodium sulphate, filtered and evaporated to yield an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR: (CDCl3, 300 MHz) 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m,3 H), 7.00 (d, 2H), 8.20 (d, 2H); M.S.: (ES+) 241 (MH+).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in saturated sodium bicarbonate solution
  3. customThe ethyl acetate layer was separated
  4. washwashed twice with saturated brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil that
  9. customslowly crystallised under high vacuum (4.79 g, 89.9%)

Quellen und Nachweise

ORD-Eintrag
ord-509b8155b009482dbfc7f082a7050417
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670368B1

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