Toluene → Ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate

HRID 370282Notes

Reaction equation

[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:13][CH2:14][O:15][CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[I-].[K+].C(O)(C)C.O>[C:17]([CH2:16][O:15][CH2:14][CH2:13][CH:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:1]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:18])[NH2:19]

Participants

Conditions

Temperature: 50 °C

Procedure

164 g (1.04 mol) of ethyl piperazinecarboxylate, 156.9 g (1.14 mol) of (2-chloroethoxy)acetamide, 241.7 g (2.28 mol) of sodium carbonate, 1 g of potassium iodide and 200 ml of toluene are introduced into a 2 1 three-necked round-bottomed flask fitted with a water-cooled condenser and a mechanical stirrer. The mixture is brought at the reflux temperature for 3 hours 30. The mixture is allowed to cool to 50° C., and 200 ml of isopropanol are added. The reaction mixture is filtered and the filtration residue is washed with 150 ml of isopropanol. The filtrate is concentrated on a rotary evaporator under reduced pressure. 272.2 g of crude product are obtained, which product is recrystallized from 500 ml of ethyl acetate. 219.2 g (81.6%) of ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate are obtained in the form of a white solid.

Workup

temperaturecooled condenser and a mechanical stirrer
filtrationThe reaction mixture is filtered
washthe filtration residue is washed with 150 ml of isopropanol
concentrationThe filtrate is concentrated on a rotary evaporator under reduced pressure
custom272.2 g of crude product are obtained
customwhich product is recrystallized from 500 ml of ethyl acetate

Sources & evidence

ORD record: ord-4dc2546bc5c343d5b5d998a7752786eb
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140501

Reaction notes

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