Dimethylformamide → HCID 66588703, compound

HRID 1092748Notes

Reaction equation

HRID 1092748 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]([CH2:20][CH2:21][CH3:22])([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].CN(C=O)C>C(OCC)C>[Br-:9].[Br-:8].[CH2:17]([N+:13]([CH2:12][CH2:11][CH3:10])([CH2:14][CH2:15][CH3:16])[CH2:20][CH2:21][CH2:22][N+:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79634-MethylpyridineHCID 86627325HCID 86627325, compound

Product 1

HCID 66588703HCID 66588703, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Methylpyridine (307 mg, 3.3 mmol), (3-bromopropyl)tripropylammonium bromide (1.0 g, 2.9 mmol), and 4 mL DMF were stirred at 100° C. in a pressure vessel for 14 h. After cooling down, the reaction mixture was added dropwise to a vigorously stirred diethyl ether (100 mL). The oily precipitates formed was collected and further purified by column chromatography (SiO2, gradient from 1:4 to 1:1 MeOH/CH2Cl2) to furnish 1-(3-tripropylammoniopropyl)-4-methylpyridinium dibromide as a colorless solid (484 mg, 38%). 1H NMR (400 MHz, CD3OD): δ 1.03 (t, J=7.0 Hz, 9 H), 1.77 (m, 6 H), 2.51 (m, 2 H), 2.70 (s, 3 H), 3.28 (m, 6 H), 3.49 (m, 2 H), 4.72 (t, J=7.8 Hz, 2 H), 7.99 (d, J=6.4 Hz, 2 H), 8.99 (d, J=6.4 Hz, 2 H); HRMS (FAB+): m/z=357.1906 [M-Br]+ (calcd for C18H34BrN2: 357.1900).

Workup

  1. temperatureAfter cooling down
  2. customThe oily precipitates
  3. customformed
  4. customwas collected
  5. customfurther purified by column chromatography (SiO2, gradient from 1:4 to 1:1 MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9a135aaa668b4d82ae9f7de62f3f6ee0
Source dataset
uspto-grants-2012_03
Patent number
US08129532B2

Reaction notes

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