(p-Acetylphenoxy)acetic acid → (4-acetylphenyloxy)-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]acetamide

HRID 1241900Notes

Reaction equation

HRID 1241900 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.Cl.[NH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:20][CH2:19]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:20][CH2:19]2)=[O:14])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 74655(p-Acetylphenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219371291-(3,4-Dichlorobenzyl)piperidin-4-ylamine dihydrochloride

Product 1

HCID 21937018(4-acetylphenyloxy)-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]acetamideYield 29.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

(4-Acetylphenyloxy)acetic acid (2.0 g) and 4-amino-1-(3,4-dichlorobenzyl)piperidine dihydrochloride (3.4 g) were suspended in DMF (50 mL), and triethylamine (2.9 mL), EDC hydrochloride (2.4 g) and HOBt (1.9 g) were added to the suspension. The suspension was stirred for 12 hrs. The reaction mixture was washed with water and then saturated brine and dried, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to crystallize to give the title compound (1.3 g) as a white solid. melting point: 113° C.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialsaturated brine and dried
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiisopropyl ether was added to the residue
  5. customto crystallize

Sources & evidence

ORD record
ord-00ced8d755e24870a4e09cd6c318c1b7
Source dataset
uspto-grants-2006_10
Patent number
US07115635B2

Reaction notes

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