Sodium Hydroxide → 5,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 401379Notes

Reaction equation

HRID 401379 reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3](O)[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>OS(O)(=O)=O>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12550011HCID 12550011, compound

Product 1

HCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepineYield 8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methyl-1-(phenylamino)-pentan-3-ol (22 g, 0.11 mol) in 98% H2SO4 (250 mL) was stirred at 50° C. for 30 min. The reaction mixture was poured into ice-water basified with sat. NaOH solution to pH 8 and extracted with CH2Cl2. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (petroleum ether) to afford 5,5-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine as a brown oil (1.5 g, 8%).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-a199b65b071f4bd6ab70abd109f0ca5f
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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