3-Chlorophenethylamine → N-[2-(3-chlorophenyl)ethyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amine

HRID 735902Notes

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].[Cl:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][NH2:34])[CH:29]=[CH:30][CH:31]=1>>[Cl:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][NH:34][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:29]=[CH:30][CH:31]=1

Participants

Reactant 2

HCID 1393813-Chlorophenethylamine

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

Product 1

HCID 67187804N-[2-(3-chlorophenyl)ethyl]-N-[4-(3-undecyl-1,2,4-oxadiazol-5-yl)benzyl]amineYield 62%

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 [2-(3-chlorophenyl)ethyl]amine gave the title compound as a colorless oil (62%). 1H NMR (CDCl3, 300 MHz) δ 7.99 (d, J=8.3 Hz, 2H, 7.37 (d, J=8.3 Hz, 2H), 7.21-6.96 (m, 4H), 3.80 (s, 2H), 2.87-2.78 (m, 2H), 2.77-2.66 (m, 4H), 1.80-1.66 (m, 2H), 1.40-1.10 (m, 16H), 0.80 (t, J=7.2 Hz, 3H). M+(LC/MS(ESI)): 468.4. HPLC (Condition A), Rt: 5.1 min (HPLC purity: 99.1%).

Workup

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

Sources & evidence

ORD record: ord-8de7647bfcf64dd09935edfe5040faff
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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