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

HRID 730699Notes

Reaction equation

HRID 730699 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-d0cb24a0527c42b2be03c7b3317efa64
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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