p-Fluoronitrobenzene → HCID 12335258, compound

HRID 1391395Notes

Reaction equation

HRID 1391395 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CN1CCCC1=O.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>O>[N:22]1([CH2:21][CH2:20][CH2:19][NH:18][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 316701-Pyrrolidinepropanamine

Product 1

HCID 12335258HCID 12335258, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 4-fluoronitrobenzene were added to a solution of 20 ml of N-methyl-pyrrolidinone, 2.18 g of N-(3-aminopropyl)pyrrolidine and 2.35 g of K2CO3. The reaction medium was heated at 60° C. for 12 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 3.3 g of N-(3-pyrrolidin-1-ylpropyl)-4-nitro-1-aminobenzene (13) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. customThe yellow precipitate formed
  3. filtrationwas filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-9422eb8fb5aa47cfb9608929f39286be
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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