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

HRID 1708631Notes

Reaction equation

HRID 1708631 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-293f3169c0194d27a02310f055f51346
Source dataset
uspto-grants-1994_10
Patent number
US05359069

Reaction notes

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