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

HRID 370282
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HRID 370282 반응식
[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]
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참가 물질

8

반응물 4

HCID 1140TolueneHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 110189312-(2-Chloroethoxy)acetamide

생성물 1

HCID 53803652Ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate수율 81.6%

시약·촉매·용매 3

HCID 4875
Potassium Iodide
촉매
HCID 962Water용매
HCID 3776Isopropanol용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4dc2546bc5c343d5b5d998a7752786eb
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06140501

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