Triethylamine → HCID 15863480, compound

Temperature

60 °C

To a solution of α-bromophenylacetic acid methyl ester, 5.0 g (22.0 mmol) in 120 mL of tetrahydrofuran was added 12 mL (88.0 mmol) of triethylamine and 5.4 g (66.0 mmol) of dimethylamine hydrochloride. The reaction mixture was heated at 60° C. in a sealed tube for three hours, cooled to ambient temperature and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water. The mixture was washed with saturated sodium bicarbonate, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography using a methanol/chloroform gradient as eluent and concentrated to dryness to yield 1.86 g (44%) of the desired isomer as a yellow oil. MS (ion spray) 193.9 (M+).

1. temperaturecooled to ambient temperature
2. concentrationconcentrated to dryness
3. customThe residue was partitioned between 20% isopropanol/chloroform and water
4. washThe mixture was washed with saturated sodium bicarbonate
5. washwashed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe residue was purified by chromatography
10. concentrationconcentrated to dryness
11. customto yield 1.86 g (44%) of the desired isomer as a yellow oil

ORD record

ord-e080f51aac6549129bee24f642fab09c

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743794B2