Reaktion #10290

Reaktionsgleichung

[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

Ausbeute 91.9%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated
2. 2
   Sonstigethe residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
3. 3
   ExtraktionThe organic solution was extracted with 5% hydrochloric acid (20 mL)
4. 4
   Waschenthe aqueous acidic phase was washed with diethyl ether
5. 5
   ExtraktionThe mixture was extracted with dichoromethane
6. 6
   Trocknenthe organic phase was dried (sodium sulfate)
7. 7
   Einengenconcentrated

Vorschrift

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%.

Quelle