反応 #10290

反応方程式

[2-(4-methoxyphenyl)-1-methylethyl]ethylamine

(2-oxo-azepan-1-yl)acetaldehyde

sodium triacetoxyborohydride

→

1-(2-{ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one

収率 91.9%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   濃縮The mixture was concentrated
2. 2
   その他the residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
3. 3
   抽出The organic solution was extracted with 5% hydrochloric acid (20 mL)
4. 4
   洗浄the aqueous acidic phase was washed with diethyl ether
5. 5
   抽出The mixture was extracted with dichoromethane
6. 6
   乾燥the organic phase was dried (sodium sulfate)
7. 7
   濃縮concentrated

実験手順

A mixture of [2-(4-methoxyphenyl)-1-methylethyl]ethylamine (0.53 g, 2.75 mmole), (2-oxo-azepan-1-yl)acetaldehyde (0.5 g, 3.2 mmole), and sodium triacetoxyborohydride (0.88 g, 4.1 mmole) in 1,2-dichloroethane (15 mL) was stirred at room temperature for 60 hours. The mixture was concentrated, and the residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The organic solution was extracted with 5% hydrochloric acid (20 mL), and the aqueous acidic phase was washed with diethyl ether and the pH was adjusted to 12 with 25% sodium hydroxide. The mixture was extracted with dichoromethane, and the organic phase was dried (sodium sulfate) and concentrated to give 1-(2-{ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one 11 (0.84 g) as a viscous oil, which was converted to the dibenzoyl-L-tartrate salt, Anal.: Calcd. for C38H46N2O10: C, 66.07; H, 6.71; N, 4.06%. Found C, 64.69; H, 6.45; N, 3.90%.

出典