Hydrochloric Acid → 3-(ethylamino)-3-Azetidinecarboxamide hydrochloride

To a suspension of 1-benzhydryl-3-ethylaminoazetidine-3-carboxylic acid amide (I-1A-6b; 36.1 g, 117 mmol) in methanol (560 ml) at room temperature was added concentrated aqueous HCl (19.5 ml, 234 mmol), resulting in a clear solution. To 20% Pd(OH)2 on carbon (3.75 g) was added methanol (85 ml), followed by the methanolic solution of I-1A-6b. The mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 20 hours. The reaction was then filtered through Celite® and concentrated to a fraction of the original volume under reduced pressure, at which point a precipitate formed. The suspension was diluted with t-butylmethyl ether (MTBE; 500 ml), stirred for an additional hour, and the precipitate collected by vacuum filtration. The solid was washed with MTBE and then dried, in vacuo, to afford I-1A-6c (24.8 g, 98%) as a colorless solid: +APcl MS (M+1) 144.1; 1H NMR (400 MHz, CD2Cl2) δ 4.56 (br s, 4H), 3.00 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

1. customresulting in a clear solution
2. customat room temperature
3. customfor 20 hours
4. filtrationThe reaction was then filtered through Celite®
5. concentrationconcentrated to a fraction of the original volume under reduced pressure, at which point a precipitate
6. customformed
7. filtrationthe precipitate collected by vacuum filtration
8. washThe solid was washed with MTBE
9. customdried, in vacuo
10. customto afford I-1A-6c (24.8 g, 98%) as a colorless solid

ORD record

ord-76b256c13ebe442c88b6ce83f91c0d92

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268133B2