Cyclopropylamine → N-cyclopropyl-N-(3-fluoro-5-nitrobenzyl)amine

HRID 1690490Notes

Reaction equation

HRID 1690490 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5]Br.[CH:13]1([NH2:16])[CH2:15][CH2:14]1>>[CH:13]1([NH:16][CH2:5][C:4]2[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:2]([F:1])[CH:3]=2)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 647705451-(Bromomethyl)-3-fluoro-5-nitrobenzene

Product 1

HCID 66906387N-cyclopropyl-N-(3-fluoro-5-nitrobenzyl)amineYield 89%

Procedure

Using an analogous procedure to that described in the third paragraph of the portion of Example 12 above that is concerned with the preparation of starting materials, 3-fluoro-5-nitrobenzyl bromide was reacted with cyclopropylamine to give N-cyclopropyl N-(3-fluoro-5-nitrobenzyl)amine in 89% yield; 1H NMR: (DMSOd6) 0.25 (m, 2H), 0.35 (m, 2H), 2.03 (m, 1H), 3.02 (br s, 1H), 3.85 (s, 2H), 7.69 (m, 1H), 7.95 (m, 1H), 8.08 (s, 1H); Mass Spectrum: M+H+: 211.

Sources & evidence

ORD record
ord-01bbfad77b1446378314621002c6b0a2
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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