Morpholine → HCID 67183151, compound

HRID 1966436Notes

Reaction equation

HRID 1966436 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][O:21][CH2:20][CH2:19]1>CN1C(=O)CCC1>[O:21]1[CH2:22][CH2:23][N:18]([C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 2386965-bromo-2-nitro-n-phenylaniline

Product 1

HCID 67183151HCID 67183151, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-nitro-N-phenylbenzenamine (0.50 g, 1.7 mmol) and morpholine (0.59 g, 6.8 mmol) in 15 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 (3×30 ml) and dried over anhydrous sodium sulfate. 5-Morpholino-2-nitro-N-phenylbenzenamine (0.42 g, 80%) was obtained by flash column chromatograph (30% acetyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.26 (t, J=5.2 Hz, 4H), 3.81 (t, J=5.2 Hz, 4H), 6.37 (d, J=2.7, 9.7 Hz, 1H), 6.45 (d, J=2.7 Hz, 1H), 7.25-7.47 (m, 5H), 8.18 (d, J=9.7 Hz, 1H), 9.87 (s, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 47.5, 66.7, 96.6, 105.9, 125.0, 126.0, 129.4, 130.2, 139.4, 145.8, 156.0.

Workup

  1. customThe reaction was quenched with 100 ml water
  2. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-04e694f190de440c8f461f064704d92b
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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