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

HRID 860763

Reaktionsgleichung

Reaktionsgleichung von HRID 860763
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH3:15][NH:16][CH3:17]>CO.CN(C=O)C>[OH:1][CH:2]([CH2:14][N:16]([CH3:17])[CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][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

4-(2,3-Epoxypropoxy)nitrobenzene (obtained as described in Synthetic Communications, 1994, 24, 833; 4.3 g,) was dissolved in methanol (30 ml) and DMF (10 ml). A solution of dimethylamine in methanol (2M, 17 ml) was added and the mixture was stirred overnight. Volatile material was removed by evaporation and the residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml). The organic layer was separated and washed with saturated sodium chloride (2×100 ml) and dried (MgSO4). Concentration gave the product as an oil that slowly crystallised under high vacuum (4.79 g, 89.9%). NMR (CDCl3): 2.33 (s, 6H), 2.98 (m, 1H), 2.54 (m, 1H), 4.00 (m, 3H), 7.00 (d, 2H), 8.20 (d, 2H); MS (M+H)+: 241.

Aufarbeitung

  1. customVolatile material was removed by evaporation
  2. customthe residue was partitioned between saturated sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-1b5988d156b64a06bc51689a4f0e14cb
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153964B2

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