Dimethyl-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]amine → [1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]dimethylamine

HRID 72193Notes

Reaction equation

HRID 72193 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([CH3:17])[CH:9]=2)[CH2:4]1>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][CH:3]([N:2]([CH3:18])[CH3:1])[CH2:4]2)=[CH:9][C:10]=1[CH3:17]

Participants

4

Reactant 1

HCID 68977058Dimethyl-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]amine

Product 1

HCID 21105349[1-(4-Amino-3-methylphenyl)pyrrolidin-3-yl]dimethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of dimethyl-[1-(3-methyl-4-nitrophenyl)pyrrolidin-3-yl]amine (200 mg) and palladium (10% on carbon, 10 mg) in methanol (10 mL) was vigorously stirred under an atmosphere of hydrogen at atmospheric pressure for 5 hours. The catalyst was then filtered off with suction and the filtrate was concentrated. The product with the molecular weight of 219.33 (C13H21N3) was obtained in this way; MS (ESI): 220 (M+H+).

Workup

  1. filtrationThe catalyst was then filtered off with suction
  2. concentrationthe filtrate was concentrated
  3. customThe product with the molecular weight of 219.33 (C13H21N3) was obtained in this way

Sources & evidence

ORD record
ord-136f90dea6354aa89f859decfb2a08a4
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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