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

HRID 2247130Notes

Reaction equation

HRID 2247130 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][NH:26][CH3:27]>C(O)C>[BrH:2].[Br-:1].[CH3:25][N: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)[CH3:27]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 23651404(3-(Dimethylamino)propyl)triphenylphosphonium bromide hydrobromideYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the teachings in EP 0235795, a suspension of 3-bromopropyltriphenylphosphonium bromide (Olo-IM4) in ethanol was reacted with 13.5 equivalents of an aqueous dimethylamine solution (50%) to provide dimethylaminopropyltriphenylphosphonium bromide HBr. After this reaction, the solvent was distilled off and the residue was recrystallized (yield: 59%).

Sources & evidence

ORD record
ord-9fba7a1b23e84769b52eb4af9364dcfe
Source dataset
uspto-grants-2010_03
Patent number
US07687646B2

Reaction notes

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