Hydrochloric Acid → HCID 20072230, compound

4-(N-Methyl-N-benzylamino)-3-hydroxybutyronitrile, 5.1 g (0.02 mole) was dissolved in 40 ml of isopropanol and 0.5 g of 5% palladium on carbon was added to the solution. The mixture was subjected to hydrogen gas under about 55 psi for 18 hr at 60° C. Mass spectrometry of a sample taken from the mixture indicated no reduction had occurred. About 2.1 ml (ca. 0.02 mole) of 37% hydrochloric acid and 0.5 g of 5% palladium on carbon were added and the mixture was subjected to hydrogen gas under 50 psi for 18 hr at room temperature. Approximately 0.02 molar equivalents of hydrogen was absorbed. A sample taken for mass spectroscopy showed product (m/e 115) and a small amount of starting material (m/e 205) unreacted. The mixture was filtered and the filtrate was concentrated to a light yellow liquid weighing 4.73 g. Proton NMR analysis showed mainly 4-methylamino-3-hydroxybutyronitrile and a small amount of starting benzyl compound and solvent was present, NMR analysis is as follows: (D2O, ppm): 4.40 (multiplet, methine proton on carbon 3), 3.20 (multiplet, methylene protons on carbon 4 bearing the protonated amino groups), 2.80 (multiplet, methylene protons on carbon 2 and methyl protons on the amino group).

1. customApproximately 0.02 molar equivalents of hydrogen was absorbed
2. filtrationThe mixture was filtered
3. concentrationthe filtrate was concentrated to a light yellow liquid

ORD record

ord-f8c82b26bee844c29ff9b23bd88d7ba4

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04990683