Dimethylamine → [3-(Dimethylamino)propyl](triphenyl)phosphanium bromide

HRID 2247134Notes

Reaction equation

[Br-].[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(Br)(=O)C>C(O)C>[Br-:2].[CH3:25][N:26]([CH3:27])[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

Conditions

Temperature: 22.5 °C

Procedure

To a stirred suspension of 3-bromopropyltriphenylphosphonium bromide (Olo-IM3) (420 g, 0.90 mol) in absolute ethanol (664 g) a solution of dimethylamine in absolute ethanol (368 g, 2.69 mol, assay: 33%) was added slowly within 30 minutes at room temperature. After complete addition the suspension was stirred 1 hour at reflux whereupon a solution was obtained. The solution was cooled to a temperature of 0-10° C. and acetyl bromide (202.7 g, 1.65 mol) was added dropwise until the pH was ≦1, and the resulting suspension was allowed to warm to 20-25° C. After the white suspension was filtered the wet product washed with absolute ethanol (237 g) and then dried under vacuum (15 h, 70° C.) to give 3-dimethylaminopropyltriphenylphosphonium bromide*HBr (Olo-IM4) as a white solid (yield: 471.2 g, 0.77 mol, 85.1%; HPLC assay: 83.2%, HPLC purity: 98.72%).

Workup

additionwas added slowly within 30 minutes at room temperature
additionAfter complete addition the suspension
temperatureat reflux whereupon a solution
customwas obtained
additionwas added dropwise until the pH was ≦1
filtrationAfter the white suspension was filtered the wet product
washwashed with absolute ethanol (237 g)
customdried under vacuum (15 h, 70° C.)

Sources & evidence

ORD record: ord-1cd04768515a4b23997e89f5c3ba1cb6
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687646B2

Reaction notes

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