Methyl iodide → 1-Methyl-1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]pyrrolidinium iodide

HRID 2228064Notes

Reaction equation

HRID 2228064 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13]([C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:22][CH:21]=4)=[O:18])=[CH:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][I:33]>CN(C=O)C>[I-:33].[CH3:32][N+:27]1([CH2:26][C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:17]([C:13]3[CH2:12][CH2:11][C:10]4[C:15](=[CH:16][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:8][CH:9]=4)[CH:14]=3)=[O:18])=[CH:25][CH:24]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10501614HCID 10501614, compound

Product 1

HCID 108404071-Methyl-1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]pyrrolidinium iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (2 ml) was dissolved 7-phenyl-N-[4—(1-pyrrolidinylmethyl)phenyl]-3,4-dihydronaphthalene-2-carboxamide (70 mg), and to the mixture was added methyl iodide (32 μl). The mixture was stirred at room temperature for 17 hours and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to give 1-methyl-1-[4—(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)benzyl]pyrrolidinium iodide (Compound 11) (78 mg) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-67a233a7ed5f428a9657bb1ed808947c
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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