2-(Piperidine-1-carbonyl)aniline → 1-[2-(2-Methyl-4-pyridinylamino)benzoyl]piperidine

HRID 64890

Reaction equation

HRID 64890 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[CH3:16][C:17]1[CH:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1>C(O)(=O)C>[CH3:16][C:17]1[CH:22]=[C:21]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([N:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:5])[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 5587302-(Piperidine-1-carbonyl)anilineHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 202358511-[2-(2-Methyl-4-pyridinylamino)benzoyl]piperidineYield 9.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 18.2 g of 1-(2-aminobenzoyl)piperidine and 12.2 g of 2-methyl-4-chloropyridine in 5.0 ml of acetic acid was heated at reflux for six hours and then kept at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue treated with dilute acid to pH 2 and extracted with methylene dichloride. The aqueous layer was made basic with potassium carbonate and extracted with chloroform. Further work-up of this solution afforded 2.58 g of 1-[2-(2-methyl-4-pyridinylamino)benzoyl]piperidine, m.p. 93°-95° C. when recrystallized from ethyl acetate--ether--hexane.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for six hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue treated
  5. additionwith dilute acid to pH 2
  6. extractionextracted with methylene dichloride
  7. extractionextracted with chloroform

Sources & evidence

ORD record
ord-3a247d4932c8499db59017a7574b9655
Source dataset
uspto-grants-1986_09
Patent number
US04610991

Linked notes

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