Acrylamide → 3-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propionamide

Triethylamine (3.60 g, 35.7 mmol) was added slowly to a solution of 3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane dihydrochloride (see Preparation B(iv) above; 5 g, 17 mmol) in ethanol (50 mL). Acrylamide (1.34 g, 18 mmol) was added to this mixture, which was then heated at reflux for 7 hours. The reaction mixture was then concentrated under reduced pressure. Water (50 mL) and sodium hydroxide (1 M, 150 mL) were added to the residue and the mixture extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a colourless solid. This was recrystallised from ethyl acetate (50 mL) to give the sub-title compound (3.80 g, 76%).

1. temperaturewas then heated
2. temperatureat reflux for 7 hours
3. concentrationThe reaction mixture was then concentrated under reduced pressure
4. additionWater (50 mL) and sodium hydroxide (1 M, 150 mL) were added to the residue
5. extractionthe mixture extracted with ethyl acetate (2×200 mL)
6. dry with materialThe combined organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give a colourless solid
10. customThis was recrystallised from ethyl acetate (50 mL)

ORD record

ord-5d38106707b14d0b9913919700d3eaec

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169921B2