Acetic Anhydride → HCID 67884582, compound

HRID 1590960Notes

Reaction equation

HRID 1590960 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([NH2:16])[CH2:10][C:9]2([CH3:18])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]1(=O)[O:24][C:22](=[O:23])[CH2:21][CH2:20]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>CC(C)=O.CN(C)C=O>[CH:1]1([O:7][N:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH:11]([N:16]3[C:22](=[O:23])[CH2:21][CH2:20][C:19]3=[O:24])[CH2:12][C:13]2([CH3:14])[CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 7922Succinic anhydrideHCID 517045Sodium AcetateHCID 222779844-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 67884582HCID 67884582, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.64 g of 1-cyclohexyloxy-4-amino-2,2,6,6-tetramethylpiperidine in 10 ml of acetone is added to a solution of 1.0 g of succinic anhydride in 25 ml of acetone. After stirring the reaction mixture at room temperature for 8 hours and removal of the solvent under reduced pressure, 3.54 g of the intermediate amide acid are obtained. A solution of the above (3.0 g), 0.1 g of sodium acetate and 3.1 ml of acetic anhydride in 10 ml of dimethylformamide is heated at 90° C. for 3 hours to effect cyclization to the desired imide. The removal of solvents under reduced pressure followed by purification utilizing SiO2 flash chromatography [heptane:ethyl acetate (60:40)] and crystallization from ethyl acetate-heptane provide the desired succinimide as a white crystalline solid m.p. 133°-36° C.

Workup

  1. customremoval of the solvent under reduced pressure, 3.54 g of the intermediate amide acid
  2. customare obtained
  3. customThe removal of solvents under reduced pressure
  4. customfollowed by purification utilizing SiO2 flash chromatography [heptane:ethyl acetate (60:40)] and crystallization from ethyl acetate-heptane

Sources & evidence

ORD record
ord-ec941db3715646559ae225099a3eeda8
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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