Hydrochloric Acid → HCID 13019465, compound

Hydrogen chloride was passed into a solution of α-(N,N-dimethylaminoethyl)benzeneacetonitrile (18.8 g) and dry methanol (6.3 ml) in dry dichloromethane (200 ml) for 8 h at 5°-15°. Solvent was removed to give a colourless oil which was taken up in dry methanol (150 ml) and treated with 2 M sodium methoxide solution (65 ml). Aminoacetaldehyde dimethyl acetal (10.6 g) was added and the mixture left to stand overnight. Methanol was then removed and the residue dissolved in 2 N hydrochloric acid (200 ml) and heated at 80° for 30 min. The mixture was cooled, adjusted to pH 9.5 with potassium carbonate and extracted with ethyl acetate (3×200 ml). The extracts were washed with brine (200 ml), concentrated and dried in vacuo to give the title compound, m.p. 135°-136° (16.3 g).

1. customSolvent was removed
2. customto give a colourless oil which
3. waitthe mixture left
4. customMethanol was then removed
5. dissolutionthe residue dissolved in 2 N hydrochloric acid (200 ml)
6. temperatureheated at 80° for 30 min
7. temperatureThe mixture was cooled
8. extractionextracted with ethyl acetate (3×200 ml)
9. washThe extracts were washed with brine (200 ml)
10. concentrationconcentrated
11. customdried in vacuo

ORD record

ord-468c024c569c4205ba18fd328bdb4182

Source dataset

uspto-grants-1982_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04324792