Phthalic Anhydride → HCID 53700405, compound

HRID 1701106Notes

Reaction equation

HRID 1701106 reaction equation
C1(=O)OC(=O)C=C1.[CH2:8]([C:10]1([CH3:21])[CH:15]([CH3:16])[CH:14]([NH2:17])[CH2:13][C:12]([CH2:19][CH3:20])([CH3:18])[NH:11]1)[CH3:9].[C:22]1(=[O:32])[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12>O1CCOCC1>[CH2:8]([C:10]1([CH3:21])[CH:15]([CH3:16])[CH:14]([NH:17][C:22](=[O:32])[C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[C:25]([OH:27])=[O:26])[CH2:13][C:12]([CH2:19][CH3:20])([CH3:18])[NH:11]1)[CH3:9]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7923Maleic Anhydride2×HCID 224860192,6-Diethyl-2,3,6-trimethylpiperidin-4-amine

Product 1

HCID 53700405HCID 53700405, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

49.0 g of maleic anhydride in 300 ml of dioxane are heated to 80° C. At this temperature 99.2 g of 2,6-diethyl-2,3,6-trimethyl-4-aminopiperidine are added dropwise in the course of 30 minutes. After a short time a light brown precipitate is formed. The reaction is continued for 1 hour at reflux temperature. The reaction mixture is then cooled to room temperature, and the precipitate is filtered off. The resultant residue is dissolved in 500 ml of warm water. A brownish solution is formed which is discoloured with active carbon, and then evaporated to dryness under vacuo. The solid residue is suspended in about 200 ml of warm ethanol, the suspension is cooled to room temperature, filtered and dried. 2,6-Diethyl-2,3,6-trimethyl-4-β-carboxy-acrylamidopiperidine (compound no. 42) is obtained: m.p. >250° C. If, instead of 49.0 g of maleic anhydride an equivalent amount of phthalic anhydride is used and otherwise the procedure described above if followed, 2,6-diethyl-2,3,6-trimethyl-4-o-carboxybenzamidopiperidine (compound no. 43 ) is obtained; m.p. 196°-197° C.

Workup

  1. customAfter a short time a light brown precipitate is formed
  2. temperatureat reflux temperature
  3. filtrationthe precipitate is filtered off
  4. dissolutionThe resultant residue is dissolved in 500 ml of warm water
  5. customA brownish solution is formed which
  6. customevaporated to dryness under vacuo
  7. temperaturethe suspension is cooled to room temperature
  8. filtrationfiltered
  9. customdried
  10. custom42) is obtained

Sources & evidence

ORD record
ord-a389e5c00c614555852005ee369d0627
Source dataset
uspto-grants-1980_03
Patent number
US04191683

Reaction notes

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