Реакция #314726

Уравнение реакции

2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol

triethylamine

4-chlorobenzenesulfonyl chloride

dimethylaminopyridine

methylcyclohexane

3,4,5-trimethoxybenzoyl chloride

→

title compound

2-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethyl 4-chlorobenzenesulfonate

Растворители

water

methylene chloride

methylene chloride

toluene

methylene chloride

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added under a nitrogen stream
2. 2
   workup.STIRRINGthe resulting mixture was stirred at 0-5° C. for 3 hours
3. 3
   ДругоеAfter completion of the reaction
4. 4
   Другоеthe resulting mixture was partitioned
5. 5
   ПромывкаThe separated organic layer was washed successively with 1N hydrochloric acid (45 ml)
6. 6
   Другоеa 5% aqueous solution of sodium hydrogencarbonate (45 ml) and water (45 ml) and evaporated to dryness
7. 7
   ДругоеSubsequently, to the residue obtained
8. 8
   Температураthe resulting mixture was heated at 40° C
9. 9
   ДругоеFurthermore, to the solution obtained
10. 10
    workup.STIRRINGthe resulting mixture was stirred at 40° C. for 30 minutes
11. 11
    workup.WAITat room temperature for 30 minutes
12. 12
    ДругоеThe crystals precipitated
13. 13
    Фильтрацияwere collected by filtration
14. 14
    Другоеdried at 50° C. in vacuo

Методика

To a mixture of 2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol (4.5 g, 16.1 mmol) and methylene chloride (45 ml), triethylamine (6.7 ml, 48.3 mmol) was added under a nitrogen stream, the resulting mixture was cooled to 0-5° C., and then a solution of 3,4,5-trimethoxybenzoyl chloride (3.8 g, 16.4 mmol) in methylene chloride (18 ml) was further added dropwise at below 10° C. After the mixture was stirred at 0-5° C. for 3 hours, dimethylaminopyridine (0.2 g, 1.6 mmol) was added dropwise at the same temperature. Subsequently, to the resulting mixture was added dropwise a solution of 4-chlorobenzenesulfonyl chloride (5.1 g, 24.2 mmol) in methylene chloride (18 ml) at below 10° C., and the resulting mixture was stirred at 0-5° C. for 3 hours. After completion of the reaction, to the reaction mixture was added water (45 ml), and the resulting mixture was partitioned. The separated organic layer was washed successively with 1N hydrochloric acid (45 ml), a 5% aqueous solution of sodium hydrogencarbonate (45 ml) and water (45 ml) and evaporated to dryness. Subsequently, to the residue obtained was added toluene to make the total volume 27 ml, and the resulting mixture was heated at 40° C. Furthermore, to the solution obtained was added methylcyclohexane (13 ml), and the resulting mixture was stirred at 40° C. for 30 minutes, and then at room temperature for 30 minutes. The crystals precipitated were collected by filtration and dried at 50° C. in vacuo to afford the title compound as a pale yellow crystalline compound.

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