Potassium Carbonate → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 2359444Notes

Reaction equation

HRID 2359444 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(Bromomethyl)-3-nitrobenzene (5 g, 23.1 mmol) was taken up in 100 mL of anhydrous THF along with pyrrolidine (2.3 mL, 27.72 mmol) and K2CO3 (4.8 g, 34.6 mmol). The reaction mixture was stirred at room temperature for 18 h and then filtered. The filtrate was concentrated under reduced pressure to afford 1-(3-nitrobenzyl)pyrrolidine. This material was taken up in 100 mL of absolute EtOH and 10% Pd on C (300 mg) was added. The resulting reaction mixture was stirred at room temperature under 1 atm of hydrogen for 18 h. The mixture was then filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 2.81 g of 3-(pyrrolidin-1-ylmethyl)aniline (70%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-167b648f3ee740929cd82ab1a1de23b1
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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