Sodium Hydroxide → 7-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2035434Notes

Reaction equation

HRID 2035434 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:19])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[I:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 100643867-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-8-iodo7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.600 g, 1.45 mmol) in methanol (20 mL) was treated with 15% aqueous NaOH (20 mL), and stirred for 3 hours at 50 C. The product mixture was diluted with water (100 mL), extracted twice with EtOAc (100 mL), the combined organic phases were washed with brine (100 mL), dried with Na2SO4 and concentrated to give 0.425 g of a yellow solid. 1H NMR (400 MHz, CDCl3) d 7.52 (s, 1 H), 6.57 (s, 1 H), 3.86 (s, 3 H), 3.12-3.06 (m, 4 H), 2.95 (m, 2 H), 2.75 (m, 1 H), 2.43 (bs, 1 H), 1.33 (d, J=8 Hz, 3 H). MS calculated for C12H16INO+H: 318, observed: 318.

Workup

  1. extractionextracted twice with EtOAc (100 mL)
  2. washthe combined organic phases were washed with brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-faf1eac24cf543eabe34cb6a6e7c3181
Source dataset
uspto-grants-2013_11
Patent number
US08575149B2

Reaction notes

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