Acetaldehyde → 2-[(2-Methoxyethyl)amino]propanenitrile

To a stirred solution of 62.4 g (0.6 mole) sodium bisulfite in 200 ml water which had been cooled in an ice bath, 26.5 g (0.6 mole) acetaldehyde were added over 5 minutes. The ice bath was removed. The reaction mixture was stirred 2.5 hours; then 45 g (0.6 mole) 2-methoxyethylamine were added (with evolution of heat). The reaction mixture was stirred 2 hours; then 39 g (0.6 mole) potassium cyanide were added with heat evolution and the resulting mixture was stirred at ambient temperature. After about 30 minutes, a second phase separated; the reaction mixture was stirred 3 hours and then allowed to stand overnight. The reaction mixture was extracted with 150 ml methylene chloride. The methylene chloride extract was dried over magnesium sulfate and stripped to give 67.4 g of the light yellow oil. The oil was distilled under vacuum to give 60.6 g of the above-identified product as a clear, colorless oil, boiling at 60° C. at 0.20 mm.

1. customThe ice bath was removed
2. temperature(with evolution of heat)
3. stirringThe reaction mixture was stirred 2 hours
4. temperaturewith heat evolution
5. stirringthe resulting mixture was stirred at ambient temperature
6. waitAfter about 30 minutes
7. customa second phase separated
8. stirringthe reaction mixture was stirred 3 hours
9. waitto stand overnight
10. extractionThe reaction mixture was extracted with 150 ml methylene chloride
11. extractionThe methylene chloride extract
12. dry with materialwas dried over magnesium sulfate

ORD record

ord-b64669c3254647e2b43dad9de6faae2c

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04602029