Hydrogen Bromide → 5-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-6-ol--hydrogen bromide (1/1)

HRID 596611Notes

Reaction equation

HRID 596611 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)O)[CH:6]=[CH:7][CH:8]=1.[BrH:21]>>[BrH:21].[OH:2][C:3]1[C:4]2[CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12][NH:11][CH2:10][CH2:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 14151509HCID 14151509, compound

Product 1

HCID 214501965-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-6-ol--hydrogen bromide (1/1)

Procedure

A solution of 3.5 g. (0.0129 mol) of N-[2-(3-methoxyphenyl)ethyl]-2-phenyl-2-hydroxyethylamine in 40 ml. of 48% hydrobromic acid is refluxed for two hours and then concentrated to dryness. The solid residue (equal mixture of 7-hydroxy and 9-hydroxy benzazepines) is chromatographed on a silica gel column, eluting with methanol in chloroform to first remove the 7-hydroxy isomer and then to yield the product 9-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, m.p. 134°-150° C. (int.).

Workup

  1. concentrationconcentrated to dryness
  2. additionThe solid residue (equal mixture of 7-hydroxy and 9-hydroxy benzazepines)
  3. customis chromatographed on a silica gel column
  4. washeluting with methanol in chloroform
  5. customto first remove the 7-hydroxy isomer

Sources & evidence

ORD record
ord-5dfade4f6c9a4d32af58bcc735d3b0a9
Source dataset
uspto-grants-1977_03
Patent number
US04011319

Reaction notes

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