Triethylamine → N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamide

HRID 2102346Notes

Reaction equation

HRID 2102346 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[OH:4].C(N(CC)CC)C.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>ClCCl>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:26](=[O:29])[CH2:27][CH3:28])=[CH:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 4239902-Amino-1-(4-benzyloxyphenyl)ethanol

Product 1

HCID 59645258N-[2-(4-benzyloxylphenyl)-2-hydroxyethyl)propionamideYield 112.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The amine from example 24 (24.8 g, 0.10 mol) was dissolved in dichloromethane (700 ml) and to this was added triethylamine (20.86 ml, 0.15 mol). The reaction mixture was stirred and cooled to 0° C., before propionyl chloride (7.12 ml, 0.082 mol) was added dropwise. The reaction mixture was then allowed to warm to room temperature over 16 hours before quenching with 3M HCl (aq) (20 ml) and water (100 ml). The reaction mixture was then extracted with dichloromethane (3×200 ml) and the combined organic layers dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a clear viscous gum (27.5 g, 0.092 mol, 90%). 1H NMR (CDCl3, 400 MHz) δ: 1.10 (t, 3H), 2.19 (q, 2H), 3.32-3.43 (m, 4H), 4.81 (s, 2H), 5.11 (m, 1H), 6.99 (d, 2H), 7.25-7.42 (m, 7H). LRMS: m/z 298 (M-H−).

Workup

  1. additionwas added dropwise
  2. custombefore quenching with 3M HCl (aq) (20 ml) and water (100 ml)
  3. extractionThe reaction mixture was then extracted with dichloromethane (3×200 ml)
  4. dry with materialthe combined organic layers dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59fb9e12a88d4c9682017f002b72990c
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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