تفاعل #1680714

معادلة التفاعل

lepidine

3-bromo-1-propanol

n-butanol water acetic acid

→

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

المذيبات

1,4-dioxane

ether

ظروف التفاعل

المعالجة

1. 1
   أخرىThe product separated as an oil
2. 2
   أخرىThe oil was crystallized from methylene chloride
3. 3
   أخرى367-mg (38%) yield

الإجراء التجريبي

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 (2H, 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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