Dimethylamine → (3-(Dimethylamino)propyl)triphenylphosphonium bromide hydrobromide

HRID 364647Notes

Reaction equation

HRID 364647 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23]Br.[CH3:25][NH:26][CH3:27]>C1(C)C(C)=CC=CC=1.C(O)C>[BrH:20].[Br-:20].[CH3:25][N:26]([CH3:27])[CH2:21][CH2:22][CH2:23][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 80011,3-DibromopropaneHCID 11776Triphenylphosphine

Product 1

HCID 23651404(3-(Dimethylamino)propyl)triphenylphosphonium bromide hydrobromideYield 88.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

There is prepared from 50 g triphenylphosphine and 38.5 g 1,3-dibrompropane in 150 ml xylene by heating for 20 hours at 130° C. under nitrogen 80 g crystalline (3-bromopropyl)-triphenylphosphoniumbromide with a melting point of 226° C. This is stirred using a solution of 33 g (0.7M) dimethylamine in 200 ml ethanol for 20 hours at 20°-25° C.) The residue is absorbed after removal of ethanol in a vacuum in 2-propanol and precipitated using hydrogen bromide gas. After recrystallization from ethanol, 43 g (3-dimethylaminopropyl)-triphenylphosphoniumbromide HBr is obtained with a melting point of 279° C.

Workup

  1. customfor 20 hours
  2. customat 20°-25° C.
  3. customis absorbed
  4. customafter removal of ethanol in a vacuum in 2-propanol
  5. customprecipitated
  6. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-02e4379f61404698b03087532058352e
Source dataset
uspto-grants-1986_08
Patent number
US04605673

Reaction notes

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