Sulfuric Acid → 9Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 741551Notes

Reaction equation

HRID 741551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16]O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 14260872(2-{[(4-Chlorophenyl)methyl]amino}phenyl)methanol

Product 1

HCID 541749289Chloro-6,11-dihydro-5H-dibenz[b,e]azepineYield 95%

Procedure

2-[[(4-chlorophenyl)methyl]amino]benzenemethanol (6.7 g) (prepared as described in J. Chem. Soc. Chem. Commun., 1989 (1), 44-5) was cooled under a N2 atmosphere to -40° C. Sulfuric acid (35 ml) was added dropwise keeping the temperature at about -10° C. and the mixture was stirred at room temperature for 1 hour. The mixture was poured into ice water and basified carefully with KOH. The mixture was filtered off and the precipitate was washed with water and CH2Cl2. The filtrate and the washings were extracted, dried with Na2SO4, filtered off and evaporated, yielding 5.8 g (95%) of 9-chloro-6,11-dihydro-5H-dibenz-[b,e]azepine (interm. 27).

Workup

  1. customat about -10° C.
  2. filtrationThe mixture was filtered off
  3. washthe precipitate was washed with water and CH2Cl2
  4. extractionThe filtrate and the washings were extracted
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered off
  7. customevaporated

Sources & evidence

ORD record
ord-a438be55064d4e95826bca58cff609d1
Source dataset
uspto-grants-1996_09
Patent number
US05552399

Reaction notes

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