Methyl iodide → 1,1-Dimethyl-2-[2-((indan-2-yl)(phenyl)amino)ethyl]pyrrolidinium iodide

HRID 538667Notes

Reaction equation

HRID 538667 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([CH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:25][I:26]>ClCCCl>[I-:26].[CH3:24][N+:20]1([CH3:25])[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][CH2:17][N:10]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68180914Indan-2-yl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]phenylamine

Product 1

HCID 601641851,1-Dimethyl-2-[2-((indan-2-yl)(phenyl)amino)ethyl]pyrrolidinium iodide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of compound 19 (0.1 g, 0.31 mmol) in DCE (3 mL) was added methyl iodide (0.058 mL, 0.94 mmol) and the resulting mixture was stirred at rt for 16 hours. The reaction mixture was concentrated under reduced pressures and the crude material was purified by column chromatography on neutral alumina eluting with 1% methanol-DCM to provide 1,1-dimethyl-2-[2-((indan-2-yl)(phenyl)amino)ethyl]pyrrolidinium iodide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressures
  2. customthe crude material was purified by column chromatography on neutral alumina eluting with 1% methanol-DCM

Sources & evidence

ORD record
ord-bb1d2ecc871a4cd4b86b9396d2ceda71
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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