Dichloromethane → 6-(2-Chloroethyl)-3-methyl-1,3-oxazinan-2-one

To a cold (ice bath) solution of 85.8 g (0.868 mole) of phosgene in 500 ml of methylene chloride was added dropwise a solution of 100 g (0.868 mole) of 4-hydroxy-1-methylpiperidine in 250 ml of methylene chloride at such a rate that the internal temperature did not exceed 12° C. A crystalline solid precipitated during addition. The mixture was stirred in the cold for 1 hr after addition was complete and then 120.8 ml (87.7 g, 0.868 mole) of triethylamine was added dropwise at such a rate that the internal temperature did not exceed 25° C. The mixture was stirred at ambient temperature overnight and then diluted with 500 ml of toluene. The methylene chloride was removed by distillation and the resultant mixture was heated at reflux for 2 hr. The mixture was cooled and treated with 500 ml of 1N hydrochloric acid. The layers were separated and the organic layer was washed successively with 500 ml of 1N hydrochloric acid, 500 ml of a 4% sodium hydroxide solution and once with brine, dried over anhydrous sodium sulfate and concentrated to give an oil as residue. The oil was subjected to vacuum distillation to give 34.4 g (22%) of clear oil (b.p. 147°-150° C. at 0.4 mm).

1. customdid not exceed 12° C
2. customA crystalline solid precipitated during addition
3. additionafter addition
4. customdid not exceed 25° C
5. stirringThe mixture was stirred at ambient temperature overnight
6. customThe methylene chloride was removed by distillation
7. temperaturethe resultant mixture was heated
8. temperatureat reflux for 2 hr
9. temperatureThe mixture was cooled
10. additiontreated with 500 ml of 1N hydrochloric acid
11. customThe layers were separated
12. washthe organic layer was washed successively with 500 ml of 1N hydrochloric acid, 500 ml of a 4% sodium hydroxide solution and once with brine
13. dry with materialdried over anhydrous sodium sulfate
14. concentrationconcentrated
15. customto give an oil as residue
16. distillationThe oil was subjected to vacuum distillation

ORD 기록

ord-180b10f607ef43f6b0eae9e38430995b

출처 데이터셋

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04886794