2-(4-(Trifluoromethyl)phenyl)propan-2-amine → N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

HRID 735914Notes

Reaction equation

HRID 735914 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].[CH3:25][C:26]([NH2:38])([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)[CH3:27]>>[CH3:27][C:26]([NH:38][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([C:15]2[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]=2)=[CH:18][CH:19]=1)([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=1)[CH3:25]

Participants

3

Reactant 2

HCID 223375792-(4-(Trifluoromethyl)phenyl)propan-2-amineHCID 865985314-(3-Undecyl-1,2,4-oxadiazol-5-yl)benzaldehyde

Product 1

HCID 67185463N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amineYield 78%

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 1-methyl-1-[4-(trifluoromethyl)phenyl]ethylamine gave the title compound as a colorless oil (78%). 1H NMR (CDCl3, 300 MHz) δ 8.07 (d, J=7.9 Hz, 2H), 7.73-7.59 (m, 4H), 7.49 (d, J=8.3 Hz, 2H), 3.57 (s, 2H), 2.80 (t, J=7.5 Hz, 2H), 1.89-1.74 (m, 2H), 1.57 (s, 3H), 1.47-1.17 (m, 19H), 0.88 (t, J=7.0 Hz, 3H). M+(LC/MS(ESI)): 516.3. HPLC (Condition A), Rt: 5.02 min (HPLC purity: 98.2%).

Workup

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

Sources & evidence

ORD record
ord-039dcfdc2ee34933a0963090de172673
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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