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

HRID 1708631ノート

反応式

HRID 1708631 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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°-126° C.

後処理

  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

出典と根拠

ORDレコード
ord-293f3169c0194d27a02310f055f51346
出典データセット
uspto-grants-1994_10
特許番号
US05359069

反応ノート

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