Piperidine → HCID 67182467, compound

HRID 1966435Notes

Reaction equation

HRID 1966435 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CN1C(=O)CCC1>[N+:15]([C:5]1[CH:4]=[CH:3][C:2]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:7][C:6]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 2386965-bromo-2-nitro-n-phenylaniline

Product 1

HCID 67182467HCID 67182467, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-bromo-2-fluoro-1-nitrobenzene (10.0 g, 45 mmol), diisopropanylethylamine (15.8 ml, 90 mmol) and aniline (5.0 ml, 54 mmol) in 100 ml 1-methylpyrrolidin-2-one (NMP) was heated at 100° C. for 16 hours. The solution was cooled to room temperature and added 1,000 ml water. The result red precipitate was filtered and washed with water (100 ml), dried under high vacuum to obtain 5-bromo-2-nitro-N-phenylbenzenamine (10.3 g, 77%). A solution of 5-bromo-2-nitro-N-phenylbenzenamine (0.50 g, 1.7 mmol) and piperidine (0.67 ml, 6.8 mmol) in 10 ml NMP was heated at 100° C. for 16 hours. The reaction was quenched with 100 ml water. The mixture was extracted with ethyl acetate (3×20 ml) and dried over anhydrous sodium sulfate. 2-Nitro-N-phenyl-5-(piperidin-1-yl)benzenamine (0.50 g, 100%) was obtained by flash column chromatograph (30% acetyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 1.66 (m, 6H), 3.33 (t, J=5.8 Hz, 4H), 6.34 (dd, J=2.6, 9.7 Hz, 1H), 6.42 (d, J=2.6 Hz, 1H), 7.23-7.46 (m, 5H), 8.14 (d, J=9.7 Hz, 1H), 9.93 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 24.8, 25.4, 48.7, 95.6, 106.4, 124.8, 125.6, 129.4, 130.1, 139.7, 146.0, 156.0.

Workup

  1. customThe reaction was quenched with 100 ml water
  2. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-374ae10b82044a7d837507ecb808a5a2
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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