Triethylamine → N-Indan-2-ylmethyl-propionamide

HRID 450728Notes

Reaction equation

HRID 450728 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1NC.[CH2:12]([N:14](CC)CC)C.[C:19]([O:23]C(=O)CC)(=O)[CH2:20][CH3:21]>C1COCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:12][NH:14][C:19](=[O:23])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31263Propionic anhydrideHCID 15023225N-Methylindan-2-amine

Product 1

HCID 67023907N-Indan-2-ylmethyl-propionamideYield 114.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of indan-2-yl-methylamine (5.55 g, 37.7 mmol) and triethylamine (5.67 g, 56.0 mmol) in 100 mL THF was stirred at 5° C. and propionic anhydride (5.15 g, 39.6 mmol) added dropwise. After the mixture was stirred for 18 h at room temperature, the solvent was removed and ethyl acetate/water were added. The organic layer was washed with water and dried over MgSO4. The filtrate was concentrated to give a brown oil (8.79 g, 97%).

Workup

  1. customthe solvent was removed
  2. additionethyl acetate/water were added
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8a3114eccd19451292f4db3d5a5a833c
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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