Sodium Hydroxide → 7-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro 1H-3-benzazepine

HRID 221288Notes

Reaction equation

HRID 221288 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([C:17]3[N:18]([CH3:22])[N:19]=[CH:20][CH:21]=3)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO>[CH3:22][N:18]1[C:17]([C:15]2[CH:14]=[CH:13][C:9]3[CH:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=3[CH:16]=2)=[CH:21][CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22292810N-Trifluoroacetyl-7-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 102434237-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro 1H-3-benzazepineYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-trifluoroacetyl-7-(2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (48 mg, 0.14 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and the solution stirred overnight at 20 C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (5 mL), dried with Na2SO4 and the solvent evaporated. Flash chromatography (0-15% MeOH in CH2Cl2, silica) resulted in 30 mg of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.48 (s, 1 H), 7.21 (m, 2 H), 7.13 (s, 1 H), 6.27 (s, 1 H), 3.89 (s, 3 H), 3.3-2.9 (m, 9 H), 2.79 (dd, J=7, 14 Hz, 1 H), 1.40 (d, J=8 Hz, 3 H). MS calculated for C15H19N3+H: 242, observed: 242.

Workup

  1. concentrationThe product mixture was concentrated
  2. extractionextracted 3 times with CH2Cl2 (5 mL)
  3. dry with materialdried with Na2SO4
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-5cf229ee51d14c6fb09906067f2dc85d
Source dataset
uspto-grants-2012_06
Patent number
US08207158B2

Reaction notes

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