(4-Nitrophenyl)acetic acid → HCID 54082859, compound

HRID 868452Notes

Reaction equation

HRID 868452 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].N1CCCCC1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH:24]1[C:29]1[CH:36]=[CH:35][C:32](C=O)=[CH:31][CH:30]=1>C(O)C>[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH:24]1[C:29]1[CH:36]=[CH:35][C:32]([CH:11]=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 53781093HCID 53781093, compound

Product 1

HCID 54082859HCID 54082859, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A one liter three necked flask fitted with a dropping funnel, mechanical stirrer, and condenser is charged with 34.35 g of 4-nitrophenylacetic acid. Piperidine (16.2 g) is added dropwise over a period of 30 minutes. At the end of the addition period, 44.46 g of 4-[N-(2-hydroxyethyl)piperazinyl]benzaldehyde is added. The mixture is heated at 100° C. for three hours, and at 130° C. for three hours. After cooling, the resultant semi-solid mass is ground up in ethanol in a blender, then filtered, washed with water, and vacuum dried. The crude solid is recrystallized from chlorobenzene: m.p. 221°-224° C.

Workup

  1. additionis added
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washwashed with water, and vacuum
  5. customdried
  6. customThe crude solid is recrystallized from chlorobenzene

Sources & evidence

ORD record
ord-e803607ca97543d1a4aa2e0c72f0d7a3
Source dataset
uspto-grants-1988_10
Patent number
US04779961

Reaction notes

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