3-Chlorophenethylamine → N-[2-(3-chlorophenyl)ethyl]-N-(4-oct-1-ynylbenzyl)amine

HRID 735909Notes

Reaction equation

[C:1]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][NH2:26])[CH:21]=[CH:22][CH:23]=1>>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][NH:26][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)[CH:21]=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 1393813-Chlorophenethylamine

HCID 136885034-(Oct-1-yn-1-yl)benzaldehyde

Product 1

HCID 67187378N-[2-(3-chlorophenyl)ethyl]-N-(4-oct-1-ynylbenzyl)amineYield 62%

Procedure

The same procedure as employed in the preparation of Example 1 (step a) but using 4-oct-1-ynylbenzaldehyde and [2-(3-chlorophenyl)ethyl]amine gave the title compound as a colorless oil (62%). 1H NMR (CDCl3, 300 MHz) δ 7.26 (d, J=8.3 Hz, 2H), 7.19-7.08 (m, 5H), 7.03-6.96 (m, 1H), 3.71 (s, 2H), 2.83-2.67 (m, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.63-1.44 to (m, 2H), 1.44-1.31 (m, 2H), 1.31-1.15 (m, 6H), 0.83 (t, J=8.3 Hz, 3H). M+(LC/MS(ESI)): 354.4. HPLC (Condition A), Rt: 4.31 min (HPLC purity: 97.5%).

Workup

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

Sources & evidence

ORD record: ord-f3c5fd49eb0a42f8bf06d6d37e1208b7
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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