4-(Trifluoromethyl)aniline → N-[4-(trifluoromethyl)phenyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

HRID 735904Notes

Reaction equation

HRID 735904 reaction equation
[CH2:1]([C:12]1[N:16]=[C:15]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[O:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1>>[F:25][C:26]([F:34])([F:35])[C:27]1[CH:28]=[CH:29][C:30]([NH:31][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([C:15]3[O:14][N:13]=[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[N:16]=3)=[CH:18][CH:19]=2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 865985314-(3-Undecyl-1,2,4-oxadiazol-5-yl)benzaldehyde

Product 1

HCID 67189245N-[4-(trifluoromethyl)phenyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amineYield 76%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzaldehyde and 4-(trifluoromethyl)aniline gave the title compound as a colorless oil (76%). 1H NMR (CDCl3, 300 MHz) δ 8.03 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.32 (d, J=8.3 Hz, 2H), 6.54 (d, J=8.3 Hz, 2H), 4.40 (s, 2H), 2.71 (t, J=7.5 Hz, 2H), 1.80-1.65 (m, 2H), 1.40-1.07 (m, 16H), 0.80 (t, J=6.8 Hz, 3H). M−(LC/MS(ESI)): 472.5; M+(LC/MS(ESI)): 474.2. HPLC (Condition A), Rt: 6.78 min (HPLC purity: 97.5%).

Workup

  1. customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record
ord-deac8d4bb4a8415d8d0b28d7eae73d04
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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