Dimethyl Sulfide → 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline

HRID 576162Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH3:17])[CH2:12][CH2:11]2)=O)=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.CSC>C1COCC1>[CH2:16]([N:13]1[CH2:14][CH2:15][N:10]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=2[C:18]([F:21])([F:19])[F:20])[CH2:11][CH2:12]1)[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of (4-amino-2-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (20 g, 66.4 mmol) in THF (500 mL) was added BH3.DMS (19.91 mL, 199 mmol) dropwise. Then the mixture was stirred at 80° C. for 4 h. The mixture was quenched by adding MeOH and then concentrated. The residue was purified by silica column chromatography on silica gel (PE:EA=2:1, Rf=0.35) to give a white solid of 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (14 g, 46.0 mmol, 69.4% yield): 1H NMR (400 MHz, CDCl3) δ: 7.48 (d, J=8.4 Hz, 1H), 6.91 (d, J=2.8 Hz, 1H), 6.79 (dd, J=2.4, 8.4 Hz, 1H), 3.76 (s, 2H), 3.53 (s, 2H), 2.45-2.39 (m, 8H), 1.08 (t, J=7.2 Hz, 3H); ES-LCMS m/z 288 (M+H).

Workup

additionwas added BH3
customThe mixture was quenched
additionby adding MeOH
concentrationconcentrated
customThe residue was purified by silica column chromatography on silica gel (PE:EA=2:1, Rf=0.35)

Sources & evidence

ORD record: ord-8bc762298fd64fc4b18584462b1c77b8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035063B2

Reaction notes

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