Sodium Hydroxide → 1-(2,6-Dichlorophenyl)piperazine

HRID 912757Notes

Reaction equation

HRID 912757 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:15]=CC=CC=1.Cl.Cl[CH2:18][CH2:19][NH:20]CCCl.[OH-].[Na+]>>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[CH2:10][CH2:15][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 848672,6-Dichloro-N-phenylanilineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 114923451-(2,6-Dichlorophenyl)piperazine

Procedure

A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1).

Workup

  1. customirradiation at 200° C. for 10 min
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic extracts were washed with brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

Sources & evidence

ORD record
ord-7739c52eccd04b9bb90ee009de2421c2
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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