HCID 57140123, compound → HCID 18007376, compound

HRID 1351895Notes

Reaction equation

HRID 1351895 reaction equation
C([N:8]([CH2:23][C@H:24]([OH:33])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[C:17]([Cl:22])[C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd].ClC1C=CC=CC=1.CO>[ClH:22].[Cl:22][C:17]1[C:18]([O:20][CH3:21])=[CH:19][C:11]2[CH2:10][CH:9]([NH:8][CH2:23][CH:24]([OH:33])[CH2:25][O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:15][CH2:14][CH2:13][C:12]=2[CH:16]=1

Participants

6

Reactant 2

HCID 57140123HCID 57140123, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18007376HCID 18007376, compoundYield 124.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of (2S)-1-[N-benzyl-N-(2-chloro-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (172 mg) and 10% palladium on activated carbon (50% wet, 50 mg) in a mixture of chlorobenzene (2 ml) and methanol (2 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 2 hours. After filtration, the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1 to 10:1) and followed by treatment with 4N hydrogen chloride in ethyl acetate to give 1-(2-chloro-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino-3-phenoxy-2-propanol hydrochloride (95 mg).

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-f995522e7d1144909f253a2ae44d5496
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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