تفاعل #72745

معادلة التفاعل

4-(2-methyl-3-(naphthalen-1-ylmethyl)-7-nitro-3H-benzo[d]imidazol-5-yl)morpholine

→

desired product

المردود 97.0%

2-methyl-6-morpholino-1-(naphthalen-1-ylmethyl)-1H-benzo[d]imidazol-4-amine

المردود 97.0%

المذيبات

H2O

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared
2. 2
   درجة الحرارةat reflux temperature overnight
3. 3
   أخرىthe solvent was removed in-vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in DCM
5. 5
   ترشيحfiltered
6. 6
   غسيلThe filtrate was then washed with brine
7. 7
   تجفيفdried over anhydrous Na2SO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in-vacuo

الإجراء التجريبي

A mixture of 4-(2-methyl-3-(naphthalen-1-ylmethyl)-7-nitro-3H-benzo[d]imidazol-5-yl)morpholine (804 mg), prepared as described in Example 2, iron powder (168 mg) and FeSO4 (84 mg) in ethanol (30 mL) and H2O (30 mL) was stirred at reflux temperature overnight. The mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was dissolved in DCM and filtered. The filtrate was then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in-vacuo to afford the desired product as a solid (720 mg, 97%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.33 (s, 3H), 2.91 (t, 4H J=4.8 Hz), 3.64 (t, 4H J=4.8 Hz), 5.15 (br s, 2H), 5.83 (s, 2H), 6.10 (d, 1H, J=2.1 Hz), 6.12 (d, 1H, J=2.1 Hz), 6.38 (d, 1H, J=7.5 Hz), 7.34 (t, 1H, J=7.5 Hz), 7.58-7.68 (m, 2H), 7.84 (d, 1H, J=8.4 Hz), 8.01 (d, 1H, J=7.5 Hz), 8.23 (d, 1H, J=8.4 Hz); LC-MS: m/e=373 [M+1]+

المصدر