HCID 22111033, compound → HCID 22111010, compound

HRID 565704Notes

Reaction equation

HRID 565704 reaction equation
[NH2:1][C:2]1[C:3]([CH3:44])=[C:4]([CH3:43])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([N:18](CC4C=CC=CC=4)[CH2:19][CH2:20][CH:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:41]=1[CH3:42].[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:3]([CH3:44])=[C:4]([CH3:43])[C:5]2[O:9][C:8]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][CH:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:14][CH2:13]3)([CH3:10])[CH2:7][C:6]=2[C:41]=1[CH3:42]

Participants

5

Reactant 2

HCID 22111033HCID 22111033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22111010HCID 22111010, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-[(5-amino-2,3dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-benzyl-N-(3,3-diphenylpropyl)-4-piperidinamine (1.5 g) in ethanol (50 mL) was added 0.30 g of 5% palladium on carbon (50% hydrous) and the mixture was stirred in a hydrogen atmosphere at 5 atmospheric pressure and 40° C. for 6 hours. This reaction mixture was filtered and the filtrate was concentrated under reduced pressure to provide 1.2 g of 1-[(5-amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-N-(3,3-diphenylpropyl)-4-piperidinamine. Yield 94%. This product was treated with 4N-HCl solution in ethanol and the resulting trihydrochloride was recrystallized from ethanol/diethyl ether to provide 1.3 g of the title compound. Yield 82%.

Workup

  1. filtrationThis reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-26467333e07a41aa8675c4b0aceaebc8
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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