Sodium Hydroxide → 8-Bromo-7-ethoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1035124Notes

Reaction equation

FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:20])[C:15]([O:17][CH2:18][CH3:19])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Br:20][C:14]1[C:15]([O:17][CH2:18][CH3:19])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-ethoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.010 g, 0.026 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred overnight at 20° C. The product mixture was diluted with water (3 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (3 mL), dried with Na2SO4 and concentrated to give 0.007 g of a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1H), 6.63 (s, 1H), 4.07 (q, J=6 Hz, 2H), 3.03 (m, 3H), 2.91 (m, 3H), 2.73 (m, 1H), 2.26 (bs, 1H), 1.46 (t, J=6 Hz, 3H), 1.32 (d, J=7 Hz, 3H). MS calculated for C15H17BrF3NO2+H: 380, observed: 380.

Workup

extractionextracted twice with EtOAc (5 mL)
washthe combined organic phases were washed with brine (3 mL)
dry with materialdried with Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-485e09af19cd430faf218b98be140592
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546378B2

Reaction notes

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