Ethanol → HCID 54691690, compound

The title compound was prepared by the general method of Southwick [J. Org. Chem. 21, 1087 (1956)]. Thus to a solution of n-pentylamine (8.04 g, 92.3 mmol) in 50 ml of dry EtOH was added ethyl acrylate (9.24 g, 92.3 mmol) with stirring under nitrogen at room temperature. After 18 h at room temperature, diethyl oxalate (13.5 g, 92.3 mmol) was added followed by a solution of sodium ethoxide in EtOH [made from sodium (2.12 g, 92.3 mmol) in 50 ml of dry EtOH]. The reaction mixture was then heated under reflux for 1 hour. To the resulting suspension was added 150 ml H2O and the reaction mixture was then concentrated under a stream of nitrogen to remove the EtOH. The white solid was then dissolved in 200 ml H2O and the solution was acidified with concentrated aqueous HCl (8.9 ml of a 10.4N solution). The resulting crystals were filtered, washed with water and dried to give the title compound (15.9 g, 71.4%) as colorless plates: mp 122°-123° C. Anal calcd for C12H19NO4 : C, 59.74; H, 7.94; N, 5.80. Found: C, 59.46; H, 7.87; N, 5.83.

1. customThe title compound was prepared by the general method of Southwick [J. Org. Chem. 21, 1087 (1956)]
2. temperatureThe reaction mixture was then heated
3. temperatureunder reflux for 1 hour
4. concentrationthe reaction mixture was then concentrated under a stream of nitrogen
5. customto remove the EtOH
6. dissolutionThe white solid was then dissolved in 200 ml H2O
7. filtrationThe resulting crystals were filtered
8. washwashed with water
9. customdried

ORD record

ord-990432f07bb1451aa98fa7cd57025817

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05202344