Ethanol → [3-(Methylamino)propyl]triphenylphosphonium Bromide Hydrobromide

HRID 58329Notes

Reaction equation

HRID 58329 reaction equation
[Br-:1].[Br:2][CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:25][NH2:26].C(O)C>>[BrH:2].[Br-:1].[CH3:25][NH:26][CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 19897074[3-(Methylamino)propyl]triphenylphosphonium Bromide HydrobromideYield 66%

Conditions

Temperature
100 °C

Procedure

(3-bromopropyl)(triphenyl)phosphonium bromide (5.7 g, 12 mmol) was treated with 33% methylamine in ethanol (40 mL, 400 mmol) in a sealed tube. The mixture was heated at 100° C. for 1.5 hours and cooled to room temperature. The volatiles were removed, and the resultant semi-solid was taken up in methanol (23 mL) and heated at 50° C., at which point all the solids dissolved. The temperature was lowered to 40° C., and methyl t-butyl ether (68 mL) was added drop wise, giving a slurry. The slurry was cooled to room temperature and filtered, washing the product cake with methyl t-butyl ether (20 mL) to afford the title compound (4.0 g) in a 66% yield as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. customThe volatiles were removed
  3. temperatureheated at 50° C., at which point all the solids
  4. dissolutiondissolved
  5. customwas lowered to 40° C.
  6. additionmethyl t-butyl ether (68 mL) was added drop wise
  7. customgiving a slurry
  8. temperatureThe slurry was cooled to room temperature
  9. filtrationfiltered
  10. washwashing the product cake with methyl t-butyl ether (20 mL)

Sources & evidence

ORD record
ord-6cdf00c7e79b4215b840b1ef063b6e51
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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