Citraconic Anhydrides → HCID 512828, compound

HRID 1016514Notes

Reaction equation

HRID 1016514 reaction equation
[C:1]1(=[O:8])O[C:5](=[O:6])[CH:4]=[C:2]1[CH3:3].[N:9]1([C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>N1C=CC=CC=1>[CH3:3][C:2]1[C:1](=[O:8])[N:19]([C:18]2[CH:17]=[CH:16][C:15]([N:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:21][CH:20]=2)[C:5](=[O:6])[CH:4]=1

Participants

4

Reactant 2

HCID 12012Citraconic AnhydridesHCID 4135014-(Piperidin-1-yl)aniline

Product 1

HCID 512828HCID 512828, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

A solution of citraconic anhydride (0. 1 M) in pyridine (20 ml)was treated with 4-(1-piperidyl)aniline (0. 1 M). The reaction mixture was heated to 90° C. for six hours. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionthe residue was extracted into ethyl acetate
  3. washThe ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid
  4. dry with materialdried over sodium sulphate
  5. concentrationfinally concentrated in vacuo
  6. customThe residue obtained
  7. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-71ff7a11642e43e8b695e9642ebc3edc
Source dataset
uspto-grants-2002_11
Patent number
US06476053B1

Reaction notes

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