HCID 27134398, compound → N-(3-Amino-4-methylphenyl)-1-pyrrolidineacetamide

HRID 1014227Notes

Reaction equation

HRID 1014227 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[N+:17]([O-])=O>C(O)C.[Pd]>[NH2:17][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:16])[CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 27134398HCID 27134398, compound

Product 1

HCID 17607979N-(3-Amino-4-methylphenyl)-1-pyrrolidineacetamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(4-methyl-3-nitrophenyl)-2-(1-pyrrolidinyl)acetamide (0.86 g, 3.27 mmol) in absolute ethanol (50 mL) was hydrogenated with 10% Pd/C (˜0.200 g, Lancaster) at 50 psi overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, and the filtrate was concentrated under reduced pressure to give N-(3-amino-4-methylphenyl)-2-(1-pyrrolidinyl)acetamide (0.72 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70 (dt, J=6.55, 3.23 Hz, 4 H) 1.95 (s, 3 H) 2.53 (t, J=5.86 Hz, 4 H) 3.13 (s, 2 H) 4,78 (s, 2 H) 6.62 (dd, J=7.87, 2.01 Hz, 1 H) 6.76 (d, J=8.06 Hz, 1 H) 6.93 (d, J=2.01 Hz, 1 H) 9.23 (s, 1 H). ESIMS (M+H)+=234.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5406a6d4c92a478aae45c698f7aebc62
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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