2-(4-(Trifluoromethyl)phenyl)propan-2-amine → N-(4-dec-1-ynylbenzyl)-N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}amine

HRID 735924Notes

Reaction equation

[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:19][C:20]([NH2:32])([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH3:21]>>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:32][C:20]([CH3:21])([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)[CH3:19])=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 2

HCID 223375792-(4-(Trifluoromethyl)phenyl)propan-2-amine

HCID 578413204-Dec-1-ynylbenzaldehyde

Product 1

HCID 67186483N-(4-dec-1-ynylbenzyl)-N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}amineYield 79%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 4-dec-1-ynylbenzaldehyde and 1-methyl-1-[4-(trifluoromethyl)phenyl]ethylamine gave the title compound as a colorless oil (79%). 1H NMR (CDCl3, 300 MHz) δ 7.74-7.57 (m, 4H), 7.36 (d, J=8.1 Hz, 2H), 7.24 (d, J=8.3 Hz, 2H), 3.48 (s, 2H), 2.41 (t, J=7.2 Hz, 2H), 1.73-1.22 (m, 18H), 0.91 (t, J=7.0 Hz, 3H). M+(LC/MS(ESI)): 430.4. HPLC (Condition A), Rt: 4.69 min (HPLC purity: 99.8%).

Workup

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

Sources & evidence

ORD record: ord-5990674ef82f4e45abc275a35ea6935f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

Loading…