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

HRID 735917Notes

Reaction equation

[CH2:1]([C:9]1[N:13]=[C:12]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[O:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH2:31])[CH:26]=[CH:27][CH:28]=1>>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH:31][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([C:12]3[O:11][N:10]=[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[N:13]=3)=[CH:15][CH:16]=2)[CH:26]=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 1393813-Chlorophenethylamine

HCID 865985324-(3-Octyl-1,2,4-oxadiazol-5-yl)benzaldehyde

Product 1

HCID 67186205N-[2-(3-chlorophenyl)ethyl]-N-[4-(3-octyl-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-octyl-1,2,4-oxadiazol-5-yl)benzaldehyde and [2-(3-chlorophenyl)ethyl]amine gave the title compound as a colorless oil (76%). 1H NMR (CDCl3, 300 MHz) δ 8.06 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H), 7.23-7.00 (m, 4H), 3.88 (s, 2H), 2.95-2.68 (m, 6H), 1.75-1.65 (m, 2H), 1.41-1.20 (m, 10H), 0.87 (t, J=7.1 Hz, 3H). M+(LC/MS(ESI)): 426.4. HPLC (Condition A), Rt: 4.35 min (HPLC purity: 99.6%).

Workup

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

Sources & evidence

ORD record: ord-627228f65be644dca881afb4fb010460
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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