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

HRID 1587862Notes

Reaction equation

HRID 1587862 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-a96f27d079e3453cb9a4d97a014665ac
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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