Реакция #44794

Уравнение реакции

sodium bicarbonate

methyl 4-[(hexahydro-1H-diazepin-1-yl)methyl]benzoate

1-(2-iodoethoxy)-4-(benzyl)benzene

triethylamine

→

methyl 4-[[hexahydro-4-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-1,4-diazepin-1-yl]methyl]benzoate

Выход 27.3%

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураat reflux for 5 hours
3. 3
   ТемператураAfter cooling
4. 4
   ЭкстракцияThe mixture was extracted with ethyl acetate
5. 5
   ПромывкаThe organic layer was washed with brine
6. 6
   Сушкаdried over sodium sulfate
7. 7
   Концентрированиеconcentrated under reduced pressure

Методика

A mixture of methyl 4-[(hexahydro-1H-diazepin-1-yl)methyl]benzoate (109 mg, 0.44 mmol) and 1-(2-iodoethoxy)-4-(benzyl)benzene (120 mg, 0.44 mmol) in THF (4 mL) was treated with triethylamine (112 μl, 0.80 mmol) and heated at reflux for 5 hours. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 55 mg of methyl 4-[[hexahydro-4-[2-[4-(phenylmethyl)phenoxy]ethyl]-1H-1,4-diazepin-1-yl]methyl]benzoate; 1H NMR (300 MHz, CDCl3) δ 7.98 (d, 2H), 7.42 (d, 2H), 7.28 (dd, 2H), 7.17 (d, 2H), 7.18 (dd, 1H), 7.09 (d, 2H), 6.82 (d, 2H), 4.05 (t, 2H), 3.92 (s, 2H), 3.91 (s, 3H), 3.69 (s, 2H), 2.97 (t, 2H), 2.88 (m, 2H), 2.84 (m, 2H), 2.69 (m, 4H), 1.81 (m, 2H) ppm.

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