Hydrochloric Acid → 1-(3-chlorophenyl)piperazin-2-one

HRID 1871188Notes

Reaction equation

HRID 1871188 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O>[Cl:20][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]2=[O:21])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22254264HCID 22254264, compound

Product 1

HCID 101311141-(3-chlorophenyl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Through a solution of Boc-protected piperazinone from Step I (17.19 g, 55.4 mmol) in 500 mL of EtOAc at -78° C. was bubbled anhydrous HCl gas. The saturated solution was warmed to 0° C., and stirred for 12 hours. Nitrogen gas was bubbled through the reaction to remove excess HCl, and the mixture was warmed to room temperature. The solution was concentrated in vacuo to provide the hydrochloride as a white powder. This material was taken up in 300 mL of CH2Cl2 and treated with dilute aqueous NaHCO3 solution. The aqueous phase was extracted with CH2Cl2 (8×300 mL) until tlc analysis indicated complete extraction. The combined organic mixture was dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled free amine as a pale brown oil.

Workup

  1. customNitrogen gas was bubbled through the reaction
  2. customto remove excess HCl
  3. temperaturethe mixture was warmed to room temperature
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-574e3b52762a40329373d28761a7eb3d
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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