2-(Dimethylamino)ethanol → N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine

HRID 1050195Notes

Reaction equation

[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].F[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-(dimethylamino)ethanol (128 mg, 1.435 mmol) in DMF (5 mL) was added to a solution of 1-fluoro-3-nitro-5-(trifluoromethyl)benzene (200 mg, 0.956 mmol) in DMF (5 mL). K2CO3 (264 mg, 1.913 mmol) was added and the mixture was stirred at 80° C. for 8 h. The mixture was cooled to rt. Then the solution was concentrated and distributed between ethyl acetate and saturated NaHCO3 solution. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.6) to yield a light yellow solid of N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine (75 mg, 0.270 mmol, 28.2% yield): 1H NMR (400 MHz, CD3OD) δ 8.22-8.02 (m, 2H), 7.72 (s, 1H), 4.43 (t, J=5.1 Hz, 2H), 3.26 (t, J=4.9 Hz, 2H), 2.78-2.60 (m, 6H). ES-LCMS m/z 279 (M+H).

Workup

temperatureThe mixture was cooled to rt
concentrationThen the solution was concentrated
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by preparative TLC (PE/EA=5:1, Rf=0.6)

Sources & evidence

ORD record: ord-fef78dfb48ca4085b72eb0b48dafd50a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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