2,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide → 2,2-diphenyl-5-[N-(4-aminomethylphenethyl)-N-methylamino]pentanamide

HRID 1463870Notes

Reaction equation

HRID 1463870 reaction equation
[C:1]1([C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)=O.CO.[Pd]>[C:26]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][NH2:25])=[CH:22][CH:23]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 1

HCID 190884772,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide

Product 1

HCID 190885182,2-diphenyl-5-[N-(4-aminomethylphenethyl)-N-methylamino]pentanamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

10% Palladium-on-carbon (0.3 g) was added to a solution of 2,2-diphenyl-5-[N-(4-cyanophenethyl)-N-methylamino]pentanamide (0.3 g--see Example 13) in 5% formic acid in methanol (21 ml). The mixture was stirred at room temperature under nitrogen for 1 hour, then filtered and the filtrate concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (2% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give an oil which crystallised on standing. The solid was triturated with ether to give the title compound as buff crystals, yield 0.1 g, m.p. 139°-142°.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give a gum which
  4. customwas purified by column chromatography on silica eluting with dichloromethane
  5. additioncontaining methanol (2% up to 10%)
  6. concentrationconcentrated in vacuo
  7. customto give an oil which
  8. customcrystallised
  9. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-eb4c6d460e174a1aa58c1facf455f0b8
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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