N-bromobutanimide → HCID 67328691, compound

HRID 1846166Notes

Reaction equation

HRID 1846166 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22])[N:6]=[C:5]([N:23]([CH3:25])[CH3:24])[CH:4]=1.[Br:26]N1C(=O)CCC1=O>C(#N)C>[Br:26][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N:23]([CH3:25])[CH3:24])=[N:6][C:7]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67328728HCID 67328728, compound

Product 1

HCID 67328691HCID 67328691, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 213 mg (0.60 mmol) of 4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyridin-2-amine in 5 mL of acetonitrile were added 107 mg (0.60 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23° C. protected from light for 3 h. The reaction mixture was poured into 50 mL of satd. aq. sodium bicarbonate and extracted two 50-mL portions of ethyl acetate. The combined organic layer was washed with one 50-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as a yellowish oil: yield 114 mg (44%); silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.29 (br m, 12H), 1.56 (quint, 2H, J=7.2 Hz), 1.68 (quint, 2H, J=7.2 Hz), 2.55 (dd, 2H, J=7.6, 7.6 Hz), 3.03 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.85 (s, 3H), 4.59 (s, 2H) and 5.76 (s, 1H); 13C NMR (CDCl3) δ 26.17, 28.08, 29.40, 29.47, 29.51, 29.57, 29.65, 29.72, 37.31, 38.05, 38.05, 55.02, 55.65, 67.87, 86.47, 96.35, 97.29, 158.80, 159.11 and 162.60; mass spectrum (APCI), m/z (M+H)+431.1913 (C20H36N2O3Br requires 431.1909).

Workup

  1. additionThe reaction mixture was poured into 50 mL of satd
  2. extractionaq. sodium bicarbonate and extracted two 50-mL portions of ethyl acetate
  3. washThe combined organic layer was washed with one 50-mL portion of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column (3×10 cm)
  7. washElution with 4:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-9b4dacd2f23e420188cd9aa6c6cab409
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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