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1-Hydroxybenzotriazole → [4-(4-acetylphenyl)phenyl]-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]acetamide

HRID 1241902
Notes
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Reaction equation

HRID 1241902 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17](O)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.Cl.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[CH2:25][CH2:24]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:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=4)[CH2:25][CH2:24]3)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21937049Akos bar-2318HCID 219371291-(3,4-Dichlorobenzyl)piperidin-4-ylamine dihydrochloride

Product 1

HCID 21937095[4-(4-acetylphenyl)phenyl]-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]acetamide
Yield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

[4-(4-Acetylphenyl)phenyl]acetic acid (2.0 g) and 4-amino-1-(3,4-dichlorobenzyl)piperidine dihydrochloride (2.5 g) were suspended in DMF (50 mL), and triethylamine (2.1 mL), EDC hydrochloride (1.6 g) and HOBt (1.3 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 (2.5 g) as a white solid. melting point: 184° 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-f37b1c1aa42949b5bffcae934c951d73
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes