Hydrochloric Acid → N-dodecyl-3,5-bis(m-trifluoromethylphenyl)4-(2-hydroxyethoxy)benzamide

HRID 1743495Notes

Reaction equation

[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.C([O:21][C:22](=O)[C:23]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:26]([O:39][CH2:40][CH2:41][OH:42])=[C:25]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:52])([F:51])[F:50])[CH:44]=2)[CH:24]=1)C.Cl>C1COCC1>[CH2:1]([NH:13][C:22](=[O:21])[C:23]1[CH:24]=[C:25]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:51])([F:52])[F:50])[CH:44]=2)[C:26]([O:39][CH2:40][CH2:41][OH:42])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

To a flame-dried flask containing dodecyl amine (0.278 g, 1.5 mmol) in THF (5 mL) cooled to −78° C. was added n-BuLi (titrated to 2.37 M in hexanes) (0.670 mL, 1.59 mmol) dropwise. The solution was stirred at −78° C. for 20 min. and then warmed to rt over 20 min. The reaction was then recooled to −40° C. and 3,5-bis-(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)-benzoic acid ethyl ester (0.215 g, 0.43 mmol) in THF (5 mL) was added. This mixture was allowed to warm to rt over 20 min. The reaction mixture was then poured into 0.1 N HCl solution and extracted with EtOAc. The combined organic layers were washed with 2 N HCl solution (3×), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:hexane) to afford N-dodecyl-3,5-bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzamide (0.254 g, 93%) as a white solid. 1H NMR (CDCl3) δ 7.90 (m, 2H); 7.82–7.76 (m, 4H); 7.65–7.56 (m, 4H); 6.22 (bt, 1H); 3.45 (dd, 2H); 3.30 (m, 4H); 1.60 (m, 2H); 1.25 (m, 18H); 0.84 (m, 3H).

Workup

temperaturewarmed to rt over 20 min
customwas then recooled to −40° C.
temperatureto warm to rt over 20 min
extractionextracted with EtOAc
washThe combined organic layers were washed with 2 N HCl solution (3×)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (30% EtOAc:hexane)

Sources & evidence

ORD record: ord-1f73d3362bc4479baa562498ef30a89b
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008636B2

Reaction notes

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