N-Ethylpiperidine → HCID 18472556, compound

HRID 565873Notes

Reaction equation

HRID 565873 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[CH2:28]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH3:29]>CN(C=O)C>[Cl-:1].[CH2:28]([N+:30]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]3[CH2:21][CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:17][CH:18]=4)[CH:13]=3)=[O:11])=[CH:5][CH:4]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH3:29]

Participants

4

Reactant 2

HCID 13007N-EthylpiperidineHCID 10809385N-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 18472556HCID 18472556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (140mg), and to the mixture was added 1-ethylpiperidine (154 μl). The mixture was stirred at room temperature for 14 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 1-ethyl-1-[4-(7-phenyl-3,4-dihydro-naphthalene-2-carboxamido)benzyl]piperidinium chloride (Compound 24) (125mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-8efb06c637cb4d4ba098e48ccb7ddf24
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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