Hydrogen Bromide → [4-(Dimethylamino)butyl](triphenyl)phosphanium bromide

HRID 1488926Notes

Reaction equation

HRID 1488926 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6]O.[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BrH:28]>C1C=CC=CC=1>[Br-:28].[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 833504-(Dimethylamino)butan-1-ol

Product 1

HCID 19764958[4-(Dimethylamino)butyl](triphenyl)phosphanium bromideYield 51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
155 °C

Procedure

Into a solution of 4-dimethylaminobutan-1-ol (2.95g, 25 mmol) and triphenylphosphine (6.55 g, 25 mmol) in benzene (20 ml) was bubbled anhydrous HBr at a moderate rate for about 10 minutes with ice bath cooling. The nearly solid white mass was removed from the cooling bath and heated to about 155° C. for about five hours (benzene distilled off at about 80° C.). After cooling to ambient temperature, water was added to the solid mass and the mixture was filtered to remove insoluble material. The acidic filtrate was extracted three times with chloroform and the aqueous layer was made basic (pH 9) with aqueous saturated NaHCO3, and then concentrated to a white solid. The solids were slurried with chloroform and removed by filtration. The filtrate was dried over magnesium sulfate, filtered, concentrated, and recrystallized from ethanol/ether (1/4). White clusters of needles were obtained and dried under vacuum to afford 5.6 g (51%) of title compound.

Workup

  1. temperaturecooling
  2. customThe nearly solid white mass was removed from the cooling bath
  3. distillation(benzene distilled off at about 80° C.)
  4. temperatureAfter cooling to ambient temperature
  5. additionwater was added to the solid mass
  6. filtrationthe mixture was filtered
  7. customto remove insoluble material
  8. extractionThe acidic filtrate was extracted three times with chloroform
  9. concentrationconcentrated to a white solid
  10. customremoved by filtration
  11. dry with materialThe filtrate was dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customrecrystallized from ethanol/ether (1/4)
  15. customWhite clusters of needles were obtained
  16. customdried under vacuum

Sources & evidence

ORD record
ord-d6fe90247f4045d482bddd60d2ca2a1c
Source dataset
uspto-grants-1997_10
Patent number
US05677287

Reaction notes

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