Reaktion #1053643

Reaktionsgleichung

lepidine

3-bromo-1-propanol

n-butanol water acetic acid

→

1-(3-Hydroxypropyl)-4-methylquinolinium bromide

Lösungsmittel

1,4-dioxane

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product separated as an oil
2. 2
   SonstigeThe oil was crystallized from methylene chloride
3. 3
   Sonstige367-mg (38%) yield

Vorschrift

A solution of lepidine (0.49 g, 3.43 mmol) and 3-bromo-1-propanol (3.1 ml, 34 mmol) in 3.0 ml of 1,4-dioxane was refluxed for 17 h. The solution was cooled to room temperature and then diluted with 30 ml of ether. The product separated as an oil and the ether layer was discarded. The oil was crystallized from methylene chloride: 367-mg (38%) yield; TLC (5:3:2, n-butanol/water/acetic acid), Rf=0.40; 1H NMR δ 9.39 (1H, d, J=6.0 Hz, aromatic), 8.57 (2H, t, J=9.1 Hz, aromatic), 8.27 (1H, t, J=7.8 Hz, aromatic), 8.05 (2H, m, aromatic), 5.08 (211, t, J=7.1 Hz, methylene), 4.81 (1H, t, J=4.9 Hz, hydroxyl), 3.51 (2H, m, methylene), 3.01 (3H, s, 4-methyl), 2.11 (2H, m, methylene). Anal. Calcd. For C13H16BrNO 0.3H2O; C, 54.29; H, 5.82; N, 4.87. Found C, 53.92; H, 5.43; N, 4.67.

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