تفاعل #720998

معادلة التفاعل

Piperidin-4-yl-carbamic acid tert-butyl ester

3-bromomethyl-6-methoxy-3,4-dihydro-2H-1-oxa-5,9-diaza-phenanthrene

N,N-diisopropylethylamine

→

1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-piperidin-4-yl-carbamic acid tert-butyl ester

المردود 87.2%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىsolvent is removed
2. 2
   استخلاصthe residue is extracted with dichloromethane (3×30 mL) and water (30 mL)
3. 3
   تجفيفThe combined organic layers are dried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىto give a residue that
7. 7
   أخرىis purified by column chromatography (silica gel, eluent: cyclohexane:ethyl acetate:methanol, 1:3:0 to 0:1:0 to 0:9:1, v/v/v)

الإجراء التجريبي

Piperidin-4-yl-carbamic acid tert-butyl ester (301 mg, 1.46 mmol, 1.0 eq) is added at room temperature to a stirred solution of 3-bromomethyl-6-methoxy-3,4-dihydro-2H-1-oxa-5,9-diaza-phenanthrene (500 mg, 1.46 mmol, 1.0 eq) in N,N-dimethylformamide (15 mL), followed by N,N-diisopropylethylamine (281 μL, 1.61 mmol, 1.1 eq). After 24 hours stirring at 80° C., solvent is removed and the residue is extracted with dichloromethane (3×30 mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: cyclohexane:ethyl acetate:methanol, 1:3:0 to 0:1:0 to 0:9:1, v/v/v) to afford [1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-piperidin-4-yl-carbamic acid tert-butyl ester as a brown viscous oil (544 mg, 74% yield).

المصدر