3-Methylbutanal → 2-Cyclopropylamino-4-methyl-pentanenitrile hydrochloride

Temperature

95 °C

Following a procedure outlined in Synth. Commun. 15 (2), 1985, 157-163, 3-methylbutyraldehyde (2.0 g) and cyclopropylamine (0.81 mL) were combined and heated to 95° C. in a pressure tube for 2 minutes. The clear, yellowish solution was cooled to RT and trimethylsilyl cyanide (2.76 mL) was added carefully over 5 minutes. The mixture was re-heated to 100° C. for 2 minutes and then allowed to cool to RT. Methanol (12 mL) was added and the mixture was heated to reflux for 12 hours. The mixture was cooled, dissolved in ethyl acetate, washed with brine, dried over Na2SO4 and evaporated. The residue was treated with HCl in dioxane (approx. 0.7 M, 30 mL) and then with ether (60 mL) with stirring. After one hour, the precipitated white solid was filtered off and dried in vacuo (1.65 g). MS (ESI): 153.4 (MH+, free base).

1. temperatureThe clear, yellowish solution was cooled to RT
2. temperatureThe mixture was re-heated to 100° C. for 2 minutes
3. temperatureto cool to RT
4. temperaturethe mixture was heated
5. temperatureto reflux for 12 hours
6. temperatureThe mixture was cooled
7. washwashed with brine
8. dry with materialdried over Na2SO4
9. customevaporated
10. additionThe residue was treated with HCl in dioxane (approx. 0.7 M, 30 mL)
11. filtrationthe precipitated white solid was filtered off
12. customdried in vacuo (1.65 g)

ORD record

ord-48a57f0c8ca14be3901b99db19177bbe

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129423B2