Hydrochloric Acid → N-[2-(3,4-Dichlorophenyl)-4-hydroxybutyl]-N-methylbenzamide

HRID 2256024Notes

Reaction equation

HRID 2256024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][O:23]C2CCCCO2)[CH2:10][N:11]([CH3:20])[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].Cl.[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][OH:23])[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22137536N-[2-(3,4-Dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]-N-methylbenzamide

Product 1

HCID 10784154N-[2-(3,4-Dichlorophenyl)-4-hydroxybutyl]-N-methylbenzamideYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butyl]-N-methylbenzamide (10.5 g) in tetrahydrofuran (100 mL) was added 6N hydrochloric acid (50 mL), and the resulting solution was allowed to stir overnight. The mixture was neutralized with 10N sodium hydroxide, diluted with water, and extracted with dichloromethane. The organic layer was dried and evaporated. The resulting yellow solid was suspended in ether and filtered to give the alcohol as a white solid (8.4 g); MS: m/z=352(M+1).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer was dried
  3. customevaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ecdc8136ef574bae9819adc71fab1a6b
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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