Triethylamine → HCID 18521579, compound

HRID 413721Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].Cl.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29](Cl)=[O:30])[CH2:25][CH2:24]1>O1CCCC1>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([NH:9][CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[O:30])[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

4.2 cm3 of triethylamine and 3.02 g of benzyl glycinate hydrochloride are added, at 20° C., to 3 g of 4-methylpiperazin-1-ylcarbonyl chloride hydrochloride in solution in 150 cm3 of tetrahydrofuran. After stirring for 16 hours at 60° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is taken up in 70 cm3 of dichloromethane. The organic phase is successively washed with twice 100 cm3 of a saturated aqueous sodium bicarbonate solution and 70 cm3 of water, and then dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.9 g of benzyl N-(4-methylpiperazin-1-ylcarbonyl)-glycinate in the form of a white solid.

Workup

concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
washThe organic phase is successively washed with twice 100 cm3 of a saturated aqueous sodium bicarbonate solution and 70 cm3 of water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-549375e81289411b85ee5f6f54d2c9a0
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569854B1

Reaction notes

Loading…