Sodium Hydroxide → HCID 53794087, compound

HRID 894467Notes

Reaction equation

HRID 894467 reaction equation
Cl[C:2]1[C:19]([O:20][CH3:21])=[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.[OH-].[Na+].[H][H]>C(O)C.O.[Pd]>[CH3:21][O:20][C:19]1[CH:2]=[CH:3][C:4]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][C@@H:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:5]=2[CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 12928524HCID 12928524, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53794087HCID 53794087, compound

Reagents, catalysts & solvents 2

HCID 23219155Palladium hydrateCatalystHCID 702EthanolSolvent

Procedure

Hydrogenate a solution of 21.10 g (0.07 moles) of (S)-7-chloro-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine (e.g. obtained as described in Example 1, step D) 3.30 g (0.0825 moles) of sodium hydroxide in 300 ml of 95% ethanol at room temperature and at 4.2 kg/cm2 (=60 psi), with 1.70 g of 20% palladium hydroxide-on-carbon until the theoretical amount of hydrogen is consumed. Remove the catalyst and concentrate the filtrate to dryness on a steam bath at about 100 mm. Stir the residue with a mixture of 100 ml of water and 150 ml of ethyl ether to total dissolution. Separate the ether layer, dry over anhydrous sodium sulfate, and evaporate to dryness. Crystallize the residue from hexane to obtain analytically pure (S)-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 50°-51° C., [α]D26 =+51.8° (c=1, ethanol).

Workup

  1. customRemove the catalyst
  2. concentrationconcentrate the filtrate to dryness on a steam bath at about 100 mm
  3. additionwith a mixture of 100 ml of water and 150 ml of ethyl ether
  4. dissolutiondissolution
  5. customSeparate the ether layer
  6. dry with materialdry over anhydrous sodium sulfate
  7. customevaporate to dryness
  8. customCrystallize the residue from hexane

Sources & evidence

ORD record
ord-f21867134f084352828f2449a19e630e
Source dataset
uspto-grants-1981_08
Patent number
US04284555

Reaction notes

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