Sodium Hydroxide → HCID 22008417, compound

HRID 1493835Notes

Reaction equation

HRID 1493835 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([OH:22])[C:19](Cl)=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>O.[Pd]>[O:1]1[C:5]2[C:6]([CH:10]3[C:16]4[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][C:15]=4[CH2:14][CH2:13][N:12]([CH3:23])[CH2:11]3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9996569HCID 9996569, compound

Product 1

HCID 22008417HCID 22008417, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

6.55 g, (0.020 mol) (+)-5-(benzofuran-7-yl)-8-chloro-7-hydroxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in 1.0N sodium hydroxide (100 ml, 0.100 mol) and water (100 ml). 10% palladium-on-carbon (3.0 g) was added, and the resulting suspension was stirred under hydrogen at 20° C. and 100 kPa for 5 days. The reaction mixture was filtered and the filtercake was thoroughly washed with 0.3N hydrochloric acid (70 ml) and methanol (135 ml). The pH of the combined filtrate and washings was brought to 8.0 and the resulting suspension was filtered. The filtercake was washed with water/methanol (1/1) and dried in vacuo at 40° C. to give 3.45 g (76% of the theoretical yield) of the desired compound as white crystals.) M.p. 227°-30° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtercake was thoroughly washed with 0.3N hydrochloric acid (70 ml) and methanol (135 ml)
  3. filtrationthe resulting suspension was filtered
  4. washThe filtercake was washed with water/methanol (1/1)
  5. customdried in vacuo at 40° C.
  6. customto give 3.45 g (76% of the

Sources & evidence

ORD record
ord-91073d8d91bf459d889bc27241450ce5
Source dataset
uspto-grants-1991_06
Patent number
US05025009

Reaction notes

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