Dimethyl oxalate → methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamate

HRID 1975570노트

반응식

HRID 1975570 반응식
[NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:4]([CH3:18])([CH3:17])[CH2:3]1.[C:19](OC)(=[O:24])[C:20]([O:22][CH3:23])=[O:21]>C1(C)C=CC=CC=1>[CH:11]1([O:10][N:5]2[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([NH:1][C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[CH2:3][C:4]2([CH3:18])[CH3:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

4

반응물 2

HCID 11120Dimethyl oxalateHCID 222779844-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

생성물 1

HCID 23372095methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamate수율 48.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 10.0 grams (39.3 mmol) of 4-amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, 27.8 grams (236 mmol) of dimethyl oxalate and 100 ml of toluene is heated at reflux. Methanol and toluene are removed from the reaction mixture by fractional distillation. The reaction is then filtered and the filtrate is concentrated to obtain a solid. Fractional crystallization of the solid from 9:1 isopropanol:methylene chloride followed by recrystallization from heptane affords 6.5 grams (48% yield) of the title compound as a white solid melting at 124°-1260° C.

후처리

  1. temperatureis heated
  2. temperatureat reflux
  3. customMethanol and toluene are removed from the reaction mixture by fractional distillation
  4. filtrationThe reaction is then filtered
  5. concentrationthe filtrate is concentrated
  6. customto obtain a solid
  7. customFractional crystallization of the solid from 9:1 isopropanol
  8. custommethylene chloride followed by recrystallization from heptane

출처 및 근거

ORD 기록
ord-68ade1f0b54545ebb89bfc2f8d6747f8
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05286865

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