Diethylamine → HCID 20272236, compound

HRID 484777Notes

Reaction equation

HRID 484777 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.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>C(O)C>[BrH:2].[Br-:1].[CH2:25]([N:27]([CH2:28][CH3:29])[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)[CH3:26]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 20272236HCID 20272236, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a one-liter 3-necked flask equipped with stirrer, condenser, addition funnel, and thermometer here was charged, 200 g of the above (3-bromopropyl)triphenylphosphonium bromide, and 650 ml ethanol. There was then added dropwise, 240 ml of diethylamine at 50° C. with stirring. After 18 hours at 65° C., the solution was concentrated to an oil and the residue was redissolved in 500 ml ethanol. The solution was again concentrated to a solid. The resulting brown solid was slurried in 500 ml of hot tetrahydrofuran and filtered. The crystal were recrystallized from tetrahydrofuran containing a small amount of ethanol to give 230 g of (3-diethylaminopropyl)triphenylphosphonium bromide hydrobromide (M.P. 239°-241° C.).

Workup

  1. customInto a one-liter 3-necked flask equipped with stirrer, condenser, addition funnel
  2. additionthermometer here was charged
  3. additionThere was then added dropwise
  4. concentrationthe solution was concentrated to an oil
  5. dissolutionthe residue was redissolved in 500 ml ethanol
  6. concentrationThe solution was again concentrated to a solid
  7. filtrationfiltered
  8. customThe crystal were recrystallized from tetrahydrofuran containing a small amount of ethanol

Sources & evidence

ORD record
ord-e9c4fead69c34d83820e56bb9cb70a11
Source dataset
uspto-grants-1985_08
Patent number
US04533722

Reaction notes

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