Methyl iodide → HCID 22153313, compound

HRID 1111087Notes

Reaction equation

HRID 1111087 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[C:16](=O)([O-])[O-].[K+].[K+].IC>CS(C)=O>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:16]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 258684-Amino-1-butanolHCID 680234-Fluorobenzaldehyde2×

Product 1

HCID 22153313HCID 22153313, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a three-neck flask fitted with a mechanical stirrer, a thermometer, and a condenser is added 124.0 g (1 mole) of 4-fluorobenzaldehyde, 89.14 g (1 mole) of 4-amino-1-butanol, and 276.4 g (2 moles) of potassium carbonate, and dimethylsulfoxide The reaction mixture is then heated at 95° C. for about 3 hours until TLC indicates no more 4-fluorobenzaldehyde is present After cooling to room temperature, the solution is chilled to -10° C., and 141.9 g (1 mole) of iodomethane is added dropwise with stirring. After 2 hours at -10° C. the solution is poured into a four-fold excess (relative to dimethylsulfoxide) of ice water, and the solid product is collected by filtration and recrystallized from water.

Workup

  1. customTo a three-neck flask fitted with a mechanical stirrer
  2. temperatureAfter cooling to room temperature
  3. temperaturethe solution is chilled to -10° C.
  4. filtrationthe solid product is collected by filtration
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-42b5362f995040c591d88a7206fd4d9a
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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