2-Amino-2-methyl-1-propanol → 2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol

HRID 1250186

Reaktionsgleichung

Reaktionsgleichung von HRID 1250186
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:12])[CH:9](Br)[CH3:10])[CH:5]=[CH:6][CH:7]=1.[NH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16]>C(#N)C.C(OCC)(=O)C>[OH:12][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[NH:13][CH:9]1[CH3:10]

Komponenten

5

Edukt 2

HCID 118072-Amino-2-methyl-1-propanolHCID 4992116alpha-Bromo-3-chloropropiophenone

Produkt 1

HCID 98379662-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3′-chloro-2-bromo-propiophenone (61.2 g, 247 mmol) in acetonitrile (752 mL) was added 2-amino-2-methyl-1-propanol (56.5 g, 630 mmol). The reaction mixture was allowed to reflux for 8 hours, then slowly cooled to room temperature. The solution was concentrated in vacuo to provide a yellow solid. The crude material was dissolved in 600 mL of ethyl acetate and washed with water (300 mL×2). The ethyl acetate layer was dried (MgSO4), filtered, and concentrated in vacuo to give the product in 90% yield. 1H NMR (CDCl3) δ0.82 (d, J=6.6 Hz, 3H), 1.07 (s, 3H), 1.39 (s, 3H), 3.19 (q, J=6.5 Hz, 1H), 3.42 (d, J=11.2 Hz, 1H), 3.83 (d, J=11.2 Hz, 2H), 7.2-7.65 (m, 4H).

Aufarbeitung

  1. temperatureto reflux for 8 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customto provide a yellow solid
  4. washwashed with water (300 mL×2)
  5. dry with materialThe ethyl acetate layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the product in 90% yield

Quellen und Nachweise

ORD-Eintrag
ord-2c2c43278f8a4941a9ec784002b51d64
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06337328B1

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