Hydrochloric Acid → HCID 68849536, compound

HRID 1292984Notes

Reaction equation

HRID 1292984 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1OC.[C:26]([O-])([O-])=[O:27].[K+].[K+].Cl>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[C:19]([O:27][CH3:26])[CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 705192-Chloro-5-nitroanisoleHCID 759941-Benzylpiperazine

Product 1

HCID 68849536HCID 68849536, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-benzylpiperazine (3.53 g, 20.0 mmol), 4-chloro-3-methoxy-nitrobenzene (3.75 g, 20.0 mmol), and K2CO3 (2.76 g, 20.0 mmol) in DMF is heated at 850 to 100° C. under nitrogen for 23 h, cooled to room temperature, treated with 2M aqueous hydrochloric acid, diluted with water and extracted with ether. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 30:70 ethyl acetate:hexanes and 50:50 ethyl acetate:hexanes as eluent) to afford the title compound as a yellow-orange oil 2.64 g (57% yield), identified by NMR analysis.

Workup

  1. extractionextracted with ether
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is chromatographed (silica gel, 30:70 ethyl acetate:hexanes and 50:50 ethyl acetate:hexanes as eluent)

Sources & evidence

ORD record
ord-db2c950da4f141b4a2d22e3457a356b2
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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