4-(Trifluoromethyl)benzylamine → N-[4-(trifluoromethyl)benzyl]-N-[4-(4-undecyl-1,3-thiazol-2-yl)benzyl]amine

HRID 735990Notes

Reaction equation

HRID 735990 reaction equation
[CH2:1]([C:12]1[N:13]=[C:14]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[S:15][CH:16]=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:36])([F:35])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[F:25][C:26]([F:35])([F:36])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([C:14]3[S:15][CH:16]=[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:13]=3)=[CH:18][CH:19]=2)=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 865985394-(4-Undecyl-1,3-thiazol-2-yl)benzaldehyde

Product 1

HCID 69002953N-[4-(trifluoromethyl)benzyl]-N-[4-(4-undecyl-1,3-thiazol-2-yl)benzyl]amineYield 90%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-(4-undecyl-1,3-thiazol-2-yl)benzaldehyde and 4-(trifluoromethyl)benzylamine gave the title compound as a colorless oil (90%). 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, 2H, J=8.3 Hz), 7.45 (d, 2H, J=8.1 Hz), 7.35 (d, 2H, J=8.1 Hz), 7.25 (d, 2H, J=8.3 Hz), 6.72 (s, 1H), 3.689 (s, 2H, J=7.3 Hz), 3.74 (s, 2H), 2.67 (t, J=2H, 7.7 Hz), 1.95-1.72 (m, 1H), 1.62-1.55 (m, 2H), 1.37-1.05 (m, 16H), 0.74 (t, 3H, J=6.7 Hz). M+(LC/MS(ESI)): 503.4. HPLC (Condition A), Rt: 4.99 min (HPLC purity: 91.2%).

Workup

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

Sources & evidence

ORD record
ord-8d2adf18e51b4b9d8ca4c767d7d74bb3
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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