Hydrochloric Acid → N-[1-[4-(1-Hydroxyethyl)phenyl]-1-methylethyl]acetamide

HRID 1282106Notes

Reaction equation

HRID 1282106 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:13][C:14](=[O:16])[CH3:15])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:13][C:14](=[O:16])[CH3:15])([CH3:11])[CH3:12])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18423181HCID 18423181, compound

Product 1

HCID 18423080N-[1-[4-(1-Hydroxyethyl)phenyl]-1-methylethyl]acetamideYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(1-(4-acetylphenyl)-1-methylethyl)acetamide (50.0 g) in methanol (400 ml) was added dropwise sodium borohydride (4.3 g) at below 5° C. over 30 min. The mixture was stirred at room temperature for 2 hr and 2N hydrochloric acid (60 ml) was added. The mixture was treated by a conventional method and the obtained crude crystals were recrystallized from ethanol to give the title compound (42.17 g) as white crystals.

Workup

  1. additionThe mixture was treated by a conventional method
  2. customthe obtained crude crystals
  3. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-3978ebd7ef4e4df7be91c7b903b62c3b
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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