N-Allyl-2,2,2-trifluoroacetamide → HCID 86635870, compound

HRID 2098537Notes

Reaction equation

HRID 2098537 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:16]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH:17]=[CH2:18]>>[CH:7]1([NH:6][CH2:5][C:4]2[CH:3]=[C:2](/[CH:18]=[CH:17]/[CH2:16][NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH:15]=[CH:14][CH:13]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 558569N-Allyl-2,2,2-trifluoroacetamideHCID 914041HCID 914041, compound

Product 1

HCID 86635870HCID 86635870, compound

Procedure

Heck coupling of N-(3-bromobenzyl)cyclohexanamine and N-allyl-2,2,2-trifluoroacetamide following the method described in Example 118 gave (E)-N-(3-(3-((cyclohexylamino)methyl)phenyl)allyl)-2,2,2-trifluoroacetamide as a colorless oil. Yield (0.20 g, 22%): 1H NMR (400 MHz, CD3OD) δ 7.55 (s, 1H), 7.48-7.50 (m, 1H), 7.42 (t, J=7.6 Hz, 1H), 7.35-7.37 (m, 1H), 6.61 (d, J=16.0 Hz, 1H), 6.32 (dt, J=16.0, 6.4 Hz, 1H), 4.19 (s, 2H), 4.05 (d, J=6.4 Hz, 2H), 3.07-3.16 (m, 1H), 2.14-2.22 (m, 2H), 1.66-1.82 (m, 2H), 1.68-1.76 (m, 1H), 1.16-1.50 (m, 5H).

Sources & evidence

ORD record
ord-a08c4ff90d084af7b7b9aa095f853809
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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