3-Chlorobenzaldehyde → N-(3-chlorobenzyl)-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

HRID 735888Notes

Reaction equation

[CH2:1]([C:12]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[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].[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH:24][CH2:23][C:20]1[CH:19]=[CH:18][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:22][CH:21]=1

Participants

Reactant 2

HCID 114773-Chlorobenzaldehyde

HCID 67187547HCID 67187547, compound

Product 1

HCID 67187722N-(3-chlorobenzyl)-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amineYield 86%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 1-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methanamine and 3-chlorobenzaldehyde gave the title compound as a colorless oil (86%). 1H NMR (DMSO-d6, 300 MHz) δ 8.03 (d, J=8.3 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.43 (s, 1H), 7.65-7.23 (m, 3H), 3.77 (s, 2H), 3.70 (s, 2H), 3.30 (s, 1H), 2.75 (t, J=7.2 Hz, 2H), 1.79-1.65 (m, 2H), 1.41-1.16 (m, 16H), 0.84 (t, J=7.0 Hz, 3H). HPLC (Condition A), Rt: 5.19 min (HPLC purity: 98.4%).

Workup

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

Sources & evidence

ORD record: ord-af3ce5d5d30f4dc0953f5985e854e947
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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