Triphenylphosphine → (3-Aminopropyl)(triphenyl)phosphonium dibromide

HRID 58333

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred, degassed solution of 3-bromopropylamine hydrobromide (25.1 g, 115 mmol) in 1-butanol (210 mL) was added triphenylphosphine (42.1 g, 160 mmol). The solution was degassed again by bubbling nitrogen through it for 10 minutes and then heated at 120° C. overnight. The solution was cooled and poured into a stirring solution of methyl t-butyl ether (700 mL) and toluene (400 mL). After stirring at room temperature until a homogenous slurry resulted, the solids were filtered and the product cake rinsed two times with methyl t-butyl ether (2×100 mL) to afford the title compound (54 g, 84%), as a white solid.

Workup

customThe solution was degassed again
customby bubbling nitrogen through it for 10 minutes
temperatureThe solution was cooled
additionpoured into a stirring solution of methyl t-butyl ether (700 mL) and toluene (400 mL)
customresulted
filtrationthe solids were filtered
washthe product cake rinsed two times with methyl t-butyl ether (2×100 mL)

Sources & evidence

ORD record: ord-ce9b76e83a664bd783d6cfab82c42e45
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434753B2

Linked notes

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