Triethylamine → HCID 22957270, compound

To a solution of racemic α-bromophenylacetic acid methyl ester, 5.0 g (22.0 mmol) in 200 mL of tetrahydrofuran was added 3.4 mL (22.0 mmol) of triethylamine and 7.3 g (66.0 mmol) of 1-methylpiperazine. The reaction mixture was refluxed for three hours, cooled to ambient temperature and concentrated to dryness. The residue was partitioned between 20% isopropano/chloroform and water. The mixture was washed with saturated sodium bicarbonate, washed with bane, dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography using a methanol/chloroform gradient as eluent. A second purification was performed using methanol/chloroform as eluent and was concentrated to dryness to yield 5.21 g (95%) of the desired mixture of isomers as a yellow oil. MS (ion spray) 249.1 (M+).

1. temperatureThe reaction mixture was refluxed for three hours
2. concentrationconcentrated to dryness
3. customThe residue was partitioned between 20%
4. washThe mixture was washed with saturated sodium bicarbonate
5. washwashed with bane
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe residue was purified by chromatography
10. customA second purification
11. concentrationwas concentrated to dryness

ORD record

ord-fb09f26577874a58a3b6edf90129df65

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743794B2