Methane → 4-[2-(1-Methoxy-ethyl)-pyrrolidin-1-ylmethyl]-phenylamine

HRID 2236502Notes

Reaction equation

HRID 2236502 reaction equation
[CH3:1][O:2][CH:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[CH3:4].C.O.NN>CO>[CH3:1][O:2][CH:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[CH3:4]

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 59300132HCID 59300132, compound

Product 1

HCID 592998924-[2-(1-Methoxy-ethyl)-pyrrolidin-1-ylmethyl]-phenylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-Methoxy-ethyl)-1-(4-nitro-benzyl)-pyrrolidine (250 mg, 0.95 mmol) is dissolved in MeOH (10 mL). To this solution is added FeCl3.6H2O (25 mg, 0.09 mmol) and active charcoal (12 mg, 1.0 mmol). The suspension is heated to reflux. Hydrazine hydrate (1.0 mL) is added, and reflux is continued for 4 h. After the mixture is cooled to room temperature, the active charcoal is filtered off through Celite, and the MeOH is removed under reduced pressure. The residue (200 mg, 90%) is used directly in the next step.

Workup

  1. temperatureThe suspension is heated to reflux
  2. temperaturereflux
  3. filtrationthe active charcoal is filtered off through Celite
  4. customthe MeOH is removed under reduced pressure

Sources & evidence

ORD record
ord-8ee4dad44a834eed9eb312ada9cd37d1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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