Sulfuric Acid → 6-chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-1-(4-methoxyphenyl)-1H-3-benzazepine

HRID 486377Notes

Reaction equation

HRID 486377 reaction equation
O[CH:2]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[C:8]=1[Cl:17].OS(O)(=O)=O>C(O)(C(F)(F)F)=O>[Cl:17][C:8]1[C:7]2[CH2:6][CH2:5][NH:4][CH2:3][CH:2]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:12]=2[CH:11]=[C:10]([O:13][CH3:14])[C:9]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 3018199N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-2-(2-chloro-3,4-dimethoxyphenyl)ethylamine

Product 1

HCID 64554486-chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-1-(4-methoxyphenyl)-1H-3-benzazepineYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7.87 g of N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-2-(2-chloro-3,4-dimethoxyphenyl)ethylamine was dissolved in 59 ml of CF3COOH. 1.7 ml of concentrated H2SO4 was added to the solution and the reaction was conducted for 4 hours. After the completion of the reaction followed by concentration under reduced pressure, 100 ml of CHCl3 and 50 ml of 10% NaOH were added to the residue to conduct extraction. The extract was washed with water, dehydrated over MgSO4 and concentrated to dryness under reduced pressure to obtain 6.25 g (yield: 83.5%) of 6-chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-1-(4-methoxyphenyl)-1H-3-benzazepine.

Workup

  1. concentrationAfter the completion of the reaction followed by concentration under reduced pressure, 100 ml of CHCl3 and 50 ml of 10% NaOH
  2. additionwere added to the residue
  3. extractionextraction
  4. washThe extract was washed with water
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9cf2b4aea8284db2b40d8336ca073cb3
Source dataset
uspto-grants-1994_03
Patent number
US05292521

Reaction notes

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