Sodium Bicarbonate → (5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

HRID 894464Notes

Reaction equation

HRID 894464 reaction equation
[Cl:1][C:2]1[C:19]([O:20]C)=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C(=O)(O)[O-].[Na+]>Br.O>[Cl:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 12928524HCID 12928524, compound

Product 1

HCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

Heat and stir a mixture of 0.850 g (0.0028 moles) of the product of step D in 12 ml of 48% hydrobromic acid at 100° C. for 16 hours. Dilute with 75 ml of water and heat on a steam bath to dissolve. Adjust to about pH 8 with solid sodium bicarbonate, filter, and wash the resulting precipitate with water. Recrystallize from ethanol to obtain analytically pure (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 188°-189° C. [α]D26 =+44.8° (c=1, dimethylformamide).

Workup

  1. temperatureHeat
  2. temperatureheat on a steam bath
  3. dissolutionto dissolve
  4. filtrationfilter
  5. washwash the resulting precipitate with water
  6. customRecrystallize from ethanol

Sources & evidence

ORD record
ord-d14dc9993e4f4300b06ae1f1669138dc
Source dataset
uspto-grants-1981_08
Patent number
US04284555

Reaction notes

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