Methyl iodide → HCID 10298678, compound

HRID 2180919Notes

Reaction equation

HRID 2180919 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:9][CH2:10][N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:7]=1.C[I:26].[C:27](#N)C>C1(C)C=CC=CC=1>[I-:26].[OH:24][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=1[C@@H:8]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:9][CH2:10][N+:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:17])[CH3:16])[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 443879Tolterodine

Product 1

HCID 10298678HCID 10298678, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
22.5 °C

Procedure

To tolterodine free base (from Example 1, 0.5 M, 2.5 ml) in toluene is added methyl iodide (1 ml). Acetonitrile (5 ml) is added to the mixture and stirred over night at 20-25° C. The solvent is removed by blowing dry nitrogen. Acetone (1 ml) and hexane (2 ml) are added and the mixture is filtered at 20-25° C. to give the title compound. Anal Calcd for C23H34INO: C, 59.10; H, 7.33; N, 3.00. Found: C, 59.00; H, 7.44; N, 3.00. The identity of the compound has been further verified and characterised by NMR analysis, mass spectrometry, and melting point determination.

Workup

  1. customThe solvent is removed
  2. additionAcetone (1 ml) and hexane (2 ml) are added
  3. filtrationthe mixture is filtered at 20-25° C.

Sources & evidence

ORD record
ord-8a226be2f8a0488dbbdfdc094f5511c0
Source dataset
uspto-grants-2005_05
Patent number
US06890920B2

Reaction notes

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