1-Amino-2-propanol → N-(2-hydroxypropyl)benzamide

HRID 915664Notes

Reaction equation

HRID 915664 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].CCN(C(C)C)C(C)C.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[OH:5][CH:3]([CH3:4])[CH2:2][NH:1][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 41-Amino-2-propanolHCID 7412Benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 10910143N-(2-hydroxypropyl)benzamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare a solution of 1-amino-2-propanol (5.0 g, 66.6 mmol) in methylene chloride (250 mL) at 0° C. under nitrogen. Add Hünig's Base (11.6 mL, 66.6 mmol) followed by benzoyl chloride (7.7 mL, 66.6 mmol). Warm the reaction mixture to room temperature and stir overnight. Wash the solution sequentially with brine (100 mL) and 1M HCl (75 mL), dry (Na2SO4), filter, and concentrate to afford 10.0 g of N-(2-hydroxypropyl)benzamide. MS: m/e=180 (MH+)

Workup

  1. washWash the solution sequentially with brine (100 mL) and 1M HCl (75 mL)
  2. dry with materialdry (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-1720d19d049141adb3d8182c3e3dac2d
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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