(4-Nitrophenyl)acetic acid → HCID 54099171, compound

HRID 1761819Notes

Reaction equation

HRID 1761819 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][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:34]=[CH:33][C:30](C=O)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1>C(O)C>[OH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:34]=[CH:33][C:30]([CH:11]=[CH:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 127174464-(4-Hydroxypiperidin-1-yl)benzaldehyde

Product 1

HCID 54099171HCID 54099171, 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, 38.4 g of 4-(4-hydroxypiperidyl)benzaldehyde is added. The reaction mixture is heated at 100° C. for three hours, and at 130° C. for three hours. After cooling, the semi-solid product mass is ground in ethanol in a blender, then filtered, washed, and vacuum dried. The crude product is recrystallized from chlorobenzene, m.p. 248°-250° C.

Workup

  1. additionis added
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washwashed
  5. customvacuum dried
  6. customThe crude product is recrystallized from chlorobenzene, m.p. 248°-250° C.

Sources & evidence

ORD record
ord-0689847027f34d8788013a56c5872d1b
Source dataset
uspto-grants-1989_05
Patent number
US04828758

Reaction notes

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