Methyl iodide → HCID 10225904, compound

HRID 2180925Notes

Reaction equation

HRID 2180925 reaction equation
[CH3:1][I:2].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:5]=1>C(#N)C.CC(C)=O>[I-:2].[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][C:6]=1[CH:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][N+:14]1([CH3:1])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 12043586HCID 12043586, compound

Product 1

HCID 10225904HCID 10225904, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl iodide (3.42 g, 1.5 mL, 0.024 mol) was added to a solution of the free base 4-methyl-2-(1-phenyl-3-piperidin-1-ylpropyl)phenol of Example 30 (0.3 g, 0.97 mmol) in a mixture of acetonitrile (6 mL) and acetone (2 mL). The reaction mixture was stirred overnight at room temperature. The solution was concentrated to initiate precipitation of the resulting quaternary ammonium salt. The white precipitate was filtered out, washed with chloroform and diethyl ether and dried under vacuum to give 0.397 g (90%) of the title compound.

Workup

  1. concentrationThe solution was concentrated
  2. customprecipitation of the resulting quaternary ammonium salt
  3. filtrationThe white precipitate was filtered out
  4. washwashed with chloroform and diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-41b9e65ce2344a08aeeb53884ac01212
Source dataset
uspto-grants-2005_05
Patent number
US06890920B2

Reaction notes

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