Methyl iodide → HCID 57964757, compound

HRID 2403533Notes

Reaction equation

HRID 2403533 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][OH:29])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:33]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][CH3:33])[CH:23]=3)[CH2:20][CH2:21]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57964712HCID 57964712, compound

Product 1

HCID 57964757HCID 57964757, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.4 g (1 mmol) of 4-{2-[4-(3-hydroxymethylphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester in 10 mL of dry dimethyl sulfoxyde is cooled at a temperature close to 5° C. and 40 mg (1 mmol) of sodium hydride (60% suspension) is added. The mixture is stirred for 30 minutes at room temperature then 140 mg (1 mmol) of iodomethane are added and stirring is maintained overnight at room temperature. The mixture is concentrated under reduced pressure. The residue is dissolved in ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.3 g (73%) of crude 4-{2-[4-(3-methoxymethylphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester which is used without purification in the next step.

Workup

  1. customclose to 5° C.
  2. stirringstirring
  3. temperatureis maintained overnight at room temperature
  4. concentrationThe mixture is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bfe63378b064143b1c8d871eff0bbc6
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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