HCID 21108381, compound → HCID 21108199, compound

HRID 1766018Notes

Reaction equation

HRID 1766018 reaction equation
[ClH:1].[C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[C:18](/[CH:21]=[CH:22]/[CH2:23][N:24]([CH3:26])[CH3:25])[CH:19]=[CH:20][C:15]=3[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[H][H]>O1CCCC1.[C].[Pd]>[ClH:1].[C:2]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[C:18]([CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH:19]=[CH:20][C:15]=3[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21108381HCID 21108381, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21108199HCID 21108199, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium-carbon (200 mg) was added to a solution of (E)-3-[1-([1,1′-biphenyl]-4-ylcarbonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl]-N,N-dimethyl-2-propen-1-amine (238 mg, 0.580 mmol) obtained in Example 2 in tetrahydrofuran, and the mixture was stirred in a hydrogen atmosphere for 1.5 days. The catalyst was filtered off, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=3:1). 4 N hydrogen chloride in ethyl acetate was added to the resultant oily matter, and the formed crystals were washed with diethyl ether, whereby the title compound (97.9 mg) was obtained as colorless powder with a mp. of 84 to 86° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent was distilled away under reduced pressure
  3. customThe resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=3:1)
  4. addition4 N hydrogen chloride in ethyl acetate was added to the resultant oily matter
  5. washthe formed crystals were washed with diethyl ether, whereby the title compound (97.9 mg)
  6. customwas obtained as colorless powder with a mp. of 84 to 86° C.

Sources & evidence

ORD record
ord-2afe8f13684b4376b4337a1f90d6b6ca
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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