Acetic Acid → 2,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amine

HRID 717616

Reaktionsgleichung

Reaktionsgleichung von HRID 717616
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][C:20](=O)[CH2:19][O:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.CCOCC>[CH3:16][C:17]1([CH3:24])[O:22][CH2:21][CH:20]([NH:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)[CH2:19][O:18]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 853464-OctylanilineHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 666148752,2-dimethyl-N-(4-octylphenyl)-1,3-dioxan-5-amineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of 4-n-octylaniline (0.205 g; 1 mmol) and 2,2-dimethyl-1,3-dioxan-5-one (Helvetica Chimica Acta, 2003, 86, 2467; 0.13 g; 1 mmol) and NaBH(OAc)3 in 1,2 dichloroethane (3.5 ml), AcOH (0.06 ml; 1 mmol) was added and the mixture was stirred for 2 h at room temperature under N2, diluted to 20 ml with Et2O and washed with 1N NaOH, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified crystallization from hexane to give the title compound (0.2 g; 63%) as a colourless solid. 1H-NMR (CDCl3) 6.97 (d, 2H, J=8.4 Hz); 6.54 (d, 2H, J=8.4 Hz); 4.1 (dd, broad s, 3H, J=4.2, 11.9 Hz); 3.74 (dd, 2H, J=4.2, 11.9 Hz); 3.4 (m, 1H); 2.47 (t, 2H, J=7.91 Hz); 1.55 (m, 2H+H2O); 1.46 (s, 3H); 1.43 (s, 3H); 1.25 (m, 10H); 0.86 (m, 3H).

Aufarbeitung

  1. additionwas added
  2. washwashed with 1N NaOH, H2O, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified
  7. customcrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-3e603cc5bb73451e8828880a2f85a777
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

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