Aniline → N-(Cyclopropylmethyl)aniline

HRID 1900269Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][CH:10]1[CH2:12][CH2:11]1.FC(F)(F)C(NC1C=CC=CC=1)=O>>[CH:10]1([CH2:9][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

Participants

Reactant 3

HCID 6115Aniline

HCID 678812,2,2-Trifluoro-N-phenylacetamide

HCID 81503Bromomethylcyclopropane

Product 1

HCID 15194687N-(Cyclopropylmethyl)aniline

Procedure

N-(Cyclopropylmethyl)aniline [NMR (200 MHz, DMSO-d6): δ0.21 (m, 2H); 0.51 (m, 2H); 1.01 (m, 1H); 3.63 (d, J=7.3 Hz, 1H); 3.80 (br s, 1H); 5.78 (br s, 1H); 7.18 (t, J=7.2 Hz, 1H); 7.25 (d, J=7.8 Hz, 2H); 7.42 (t, J=7.3 Hz, 2H)] was prepared from aniline and (bromomethyl)cyclopropane via trifluoroacetanilide using the general method described by Hodge (Harland, P. A.; Hodge, P; Maughan, W.; Wildsmith, E. Synthesis, 1984, 941.).

Workup

customSynthesis, 1984, 941

Sources & evidence

ORD record: ord-8e90747b950249c7911fdbb5ab785b1d
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574159

Reaction notes

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