Methyl iodide → N-[2-(3,4-Dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]-N-methylbenzamide

HRID 2256023Notes

Reaction equation

HRID 2256023 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:10][NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[K+].I[CH3:32]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:10][N:11]([CH3:32])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 22137538N-[2-(3,4-Dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]benzamide

Product 1

HCID 22137536N-[2-(3,4-Dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of N-[2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]benzamide (3.3 g) in dimethyl sulfoxide (20 mL) was added powdered potassium hydroxide (1.6 g), followed by iodomethane (1.0 mL) after 15 minutes. After 1 hour, the mixture was diluted with water (330 mL) and extracted with dichloromethane. The combined organic extracts were dried and evaporated to give the N-methylbenzamide (3.1 g) as an oil; MS: m/z=352[(M+1)-tetrahydropyranyl].

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-fb16bd431abe43f98994f798f752b696
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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