Methylamine → N,N'-dimethylphthalamide

HRID 1699964Notes

Reaction equation

[Br-].[C:2]1(=[O:29])[N:6]([CH2:7]CC[N+](CCCNC(OC(C)(C)C)=O)(C)C)[C:5](=[O:24])[C:4]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:3]12.[CH3:30][NH2:31]>>[CH3:30][NH:31][C:5](=[O:24])[C:4]1[C:3](=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]([NH:6][CH3:7])=[O:29]

Participants

Reactant 2

HCID 6329Methylamine

HCID 70002463HCID 70002463, compound

Product 1

HCID 5237652N,N'-dimethylphthalamide

Procedure

N-(phthalimidopropyl)-N-((t-butoxycarbonylamino)propyl)-N,N-dimethylammonium bromide [1.6] (4.1 g, 0.87 mmol) was dissolved in ethanolic methylamine (33 wt %, 8.02M, 10 ml). The colourless solution was stirred at room temperature for 3 days, during which time a thick white precipitate formed (N,N′-dimethylphthalamide). The mixture was filtered; the solid was washed with a little cold ethanol. The filtrate was evaporated under reduced pressure to give an oil; this was triturated with ether and dried under high vacuum to give the title compound [1.7] as a foam. Used without further purffication.

Sources & evidence

ORD record: ord-cf80383a58024f10ad61a10e4f4b84a2
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348599B1

Reaction notes

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