4-Methylpyridine → HCID 66588673, compound

HRID 1092747Notes

Reaction equation

HRID 1092747 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Br-:8].[Br:9][CH2:10][CH2:11][CH2:12][N+:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15]>CN(C=O)C>[Br-:9].[Br-:8].[CH2:14]([N+:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:12][CH2:11][CH2:10][N+:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:15]

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 135522003-Bromo-N,N,N-triethylpropan-1-aminium bromide

Product 1

HCID 66588673HCID 66588673, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methylpyridine (307 mg, 3.3 mmol), (3-bromopropyl)triethylammonium bromide (1.0 g, 3.3 mmol), and 4 mL DMF were stirred at 100° C. in a pressure vessel for 41 h. Precipitates formed during the reaction. After cooling down, the precipitates were filtered out and washed with CH2Cl2 to give 1-(3-triethylammoniopropyl)-4-methylpyridinium dibromide as a light pink solid (750 mg, 57%), which was used in the next aldol condensation without further purification. 1H NMR (400 MHz, CD3OD): δ 1.34 (t, J=7.0 Hz, 9 H), 2.50 (m, 2 H), 2.70 (s, 3 H), 3.35-3.47 (m, 8 H), 4.73 (t, J=7.8 Hz, 2 H), 7.99 (d, J=6.4 Hz, 2 H), 8.98 (d, J=6.4 Hz, 2 H); 13C NMR (100 MHz, CD3OD): δ 8.0, 22.1, 25.2, 54.4, 54.5, 58.3, 130.1, 145.2, 161.9; HRMS (FAB+): m/z=315.1428 [M-Br]+ (calcd for C15H28BrN2: 315.1430).

Workup

  1. customPrecipitates
  2. customformed during the reaction
  3. temperatureAfter cooling down
  4. filtrationthe precipitates were filtered out
  5. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-994d0aaeb81e4f9db230e31566b9ee3e
Source dataset
uspto-grants-2012_03
Patent number
US08129532B2

Reaction notes

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