N-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide → HCID 18472479, compound

HRID 1277057Notes

Reaction equation

HRID 1277057 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.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]1>CN(C=O)C>[Cl-:1].[CH2:38]([O:37][C:35]([CH:32]1[CH2:33][CH2:34][N+:29]([CH3:28])([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)[CH2:30][CH2:31]1)=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 10809385N-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamideHCID 11062856Ethyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 18472479HCID 18472479, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3 ml) was dissolved N-[4-(chloromethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (150 mg), and to the mixture was added ethyl 1-methylpiperidine-4-carboxylate (206 mg). The mixture was stirred at room temperature for 15 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 4-ethoxycarbonyl-1-methyl-1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]piperidinium chloride (Compound 31) (185 mg, ratio of isomers=37:63) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-4e91a2f27b9244e9a6b0808fa2e4c25b
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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