Hydrochloric Acid → 1-(2-Chloroethyl)-4-(4-nitrophenyl)piperazine

HRID 2117627Notes

Reaction equation

HRID 2117627 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[ClH:19]>C(Cl)Cl.CCOCC>[Cl:19][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27639362-(4-(4-Nitrophenyl)piperazin-1-yl)ethanol

Product 1

HCID 117711831-(2-Chloroethyl)-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-Hydroxyethyl)-4-(4-nitrophenyl)piperazine (5 g, 0.02 mol) was dissolved in 50 mL of DCM and treated with HCl (40 mL of a 1M solution in Et2O) under a drying tube for 90 min. The solvent was evaporated, the residue dissolved in thionyl chloride (60 mL) and the mixture refluxed at 80° C. After 5 h, the reaction was complete as shown by LCMS and the thionyl chloride was removed under reduced pressure redissolving in DCM and evaporating three times to give the title compound as the HCl salt. LCMS: 93%, t=0.88 min, [MH+]=270.23.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in thionyl chloride (60 mL)
  3. customthe thionyl chloride was removed under reduced pressure
  4. dissolutionredissolving in DCM
  5. customevaporating three times

Sources & evidence

ORD record
ord-f4b3700b07da4dc4be0eec41c7748983
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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