Triethylamine → N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 900961Notes

Reaction equation

HRID 900961 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>ClCCl>[CH2:1]([C:3]1[N:8]=[C:7]([NH:9][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 890216-Ethylpyridin-2-amine

Product 1

HCID 45094816N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-ethyl-pyridin-2-ylamine (20 g, 0.164 mol) and triethylamine (29.6 mL, 0.213 mol) in dichloromethane (200 mL, 0.8 M) is cooled to 0° C. and carefully treated with pivaloyl chloride (26.2 mL, 0.213 mol). After stirring for 2 h, the solution is quenched with aq NaHCO3, extracted with dichloromethane and concentrated. The resulting oil is filtered through a plug of silica gel using ethyl acetate. The filtrate is concentrated and triterated with heptane to give N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (18.3 g, 54%) as a white crystalline solid. mp 59-62° C.; Rf 0.31 (25% ethyl acetate in hexanes); 1H NMR (DMSO-d6, 300 MHz) δ 9.56 (s, 1 H), 7.85 (d, J=8.4 Hz, 1 H), 7.63 (t, J=7.8 Hz, 1 H), 6.93 (d, J=7.5 Hz, 1 H), 2.65 (q, J=7.8 Hz, 2 H), 1.20 (s, 9 H), 1.18 (t, 7.8 Hz, 3 H); LRMS calcd for C12H18N2O: 206.2; found 206.0 (M)+. Anal. Calcd for C12H18N2O: C, 69.87; H, 8.80; N, 13.58. Found C, 69.60; H, 8.67; N, 13.42.

Workup

  1. customthe solution is quenched with aq NaHCO3
  2. extractionextracted with dichloromethane
  3. concentrationconcentrated
  4. filtrationThe resulting oil is filtered through a plug of silica gel
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-33c22a6a36e14ad493d70fa699deeea4
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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