Hydrochloric Acid → HCID 65383228, compound

HRID 521373Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:16]#[N:17])=[CH:10][CH:9]=1.Cl>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH2:16][NH2:17])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium aluminum hydride (52.9 mL, 52.9 mmol) in THF (1.0M) was added to a solution of 2-(4-bromophenylamino)-2-(4-chlorophenyl)acetonitrile (20.0 g, 62.2 mmol) in THF (311 mL, 62.2 mmol) at −78° C. The reaction was allowed to stir at −78° C. and gradually warmed to room temperature over 4 hours. The reaction mixture was poured into 1N HCl. The solution was then basified and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried and concentrated to give an oil. This residue was purified by column chromatography, eluting first with ethyl acetate/hexanes (2:1) then 5% MeOH/CH2Cl2→10% MeOH/CH2Cl2+1% NH4OH, affording N1-(4-bromophenyl)-1-(4-chlorophenyl)ethane-1,2-diamine as an oil (9.60 g, 49%). 1H NMR (400 MHz, CD3OD) δ □7.38 (d, 2H), 7.34 (d, 2H), 7.15 (d, 2H), 6.53 (d, 2H), 4.59 (dd, J=9.8, 4.7 Hz, 1H), 3.14 (dd, J=12.9, 4.7 Hz, 1H), 3.05 (dd, J=12.9, 9.4 Hz, 1H).

Workup

temperaturegradually warmed to room temperature over 4 hours
extractionextracted with ethyl acetate (3×)
washThe combined organic layers were washed with brine
customdried
concentrationconcentrated
customto give an oil
customThis residue was purified by column chromatography
washeluting first with ethyl acetate/hexanes (2:1)

Sources & evidence

ORD record: ord-c704697be662406d9c55630241972d6c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328091B2

Reaction notes

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