Acetic Acid → 1-(5-chloropyrimidin-2-yl)-N-cyclopropylpiperidin-4-amine

1-(5-Chloropyrimidin-2-yl)piperidin-4-one (1.5 g) is dissolved in anhydrous dichloromethane (25 mL) and cyclopropylamine (0.42 g) is added followed by glacial acetic acid (0.80 mL). Sodium triacetoxyborohydride (1.8 g) is then added in one portion under nitrogen and the resulting mixture stirred at r.t. for 17 h. The mixture is diluted with dichloroemthane (25 mL) and extracted with 3 M HCl (75 mL and 50 mL). The combined HCI layers are cooled on ice and 4 M NaOH (100 mL) is added in portions until the mixture is strongly basic (pH ˜14). The mixture is then extracted with dichloroemthane (150 mL and 100 mL) and the combined dichloromethane layers are dried over Na2SO4, filtered and concentrated to yield the title compound. LC (method 21): tR=2.57 min; Mass spectrum (APCI): m/z=253 [M+H]+.

1. additionThe mixture is diluted with dichloroemthane (25 mL)
2. extractionextracted with 3 M HCl (75 mL and 50 mL)
3. temperatureThe combined HCI layers are cooled on ice and 4 M NaOH (100 mL)
4. additionis added in portions until the mixture
5. extractionThe mixture is then extracted with dichloroemthane (150 mL and 100 mL)
6. dry with materialthe combined dichloromethane layers are dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-65f4f01b870f4d55893b13e90d4903aa

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08921398B2