Hydrochloric Acid → 8-Bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 967269Notes

Reaction equation

HRID 967269 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:20])[C:17]([OH:19])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+].Cl>CO>[Br:20][C:16]1[C:17]([OH:19])=[CH:18][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]=2[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22292823N-Trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 104690838-Bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.018 g, 0.047 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred for 3 hours at 50 C. The product mixture was brought to pH 7-8 with 10% aqueous HCl, extracted three times with EtOAc (50 mL), dried with MgSO4, and concentrated to give 0.013 g of a white solid. 1H NMR (400 MHz, CD3OD) d 7.10 (s, 1 H), 6.60 (s, 1 H), 3.30 (m, 1H), 3.2−3.0 (m, 2 H), 2.78 (m, 1H), 2.7−2.5 (m, 2H), 2.3−2.1 (m, 2 H), 1.05 (d, 3 H), 0.73 (d, 3 H). MS calculated for C13H18BrNO+H: 284, observed: 284.

Workup

  1. extractionextracted three times with EtOAc (50 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab3e3e3527cd411eaf7fa64f46c8ba23
Source dataset
uspto-grants-2005_10
Patent number
US06953787B2

Reaction notes

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