Triethylamine → 2-Methyl-N-(4-nitrophenyl)-1-piperidinepropanamine

HRID 1391397Notes

Reaction equation

HRID 1391397 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.[CH3:18][CH:19]1[N:24]([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>O>[CH3:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][CH2:27][NH:28][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 5202111-(3-Aminopropyl)-2-pipecoline

Product 1

HCID 430804522-Methyl-N-(4-nitrophenyl)-1-piperidinepropanamineYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2 g of para-fluoronitrobenzene were added to a solution of 20 ml of N-methyl-pyrrolidinone, 1.65 g of 1-(3-aminopropyl)-2-pipecoline and 1.72 g of triethylamine. The reaction medium was heated at 60° C. for 8 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. 2.2 g of N-[3-(2-methyl-piperidin-1-yl)propyl]-4-nitro-1-aminobenzene (17) 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-340791f9f2ad4d088307e2d280096adc
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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