4-Bromobenzylamine → N-(4-bromobenzyl)-N-(4-oct-1-ynylbenzyl)amine

HRID 735922Notes

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].[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>>[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][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:20][CH:19]=1

Participants

Reactant 2

HCID 775714-Bromobenzylamine

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

Product 1

HCID 67186446N-(4-bromobenzyl)-N-(4-oct-1-ynylbenzyl)amineYield 86%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-oct-1-ynylbenzaldehyde and 4-bromobenzylamine gave the title compound as a colorless oil (86%). 1H NMR (CDCl3, 300 MHz) δ 7.47 (d, J=8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 7.30-7.19 (m, 4H), 3.78 (s, 2H), 3.75 (s, 2H), 2.42 (t, J=6.8 Hz, 2H), 1.69-1.55 (m, 2H), 1.54-1.42 (m, 2H), 1.42-1.27 (m, 4H), 0.93 (t, J=6.8 Hz, 3H). M+(LC/MS(ESI)): 384.4 HPLC (Condition A), Rt: 4.18 min (HPLC purity: 97.6%).

Workup

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

Sources & evidence

ORD record: ord-9ff5cfca6596497d9a793f058b68fa81
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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