Trifluoroacetic acid → 1-(4-Chlorophenyl)piperazine

HRID 716889Notes

Reaction equation

HRID 716889 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 63789403HCID 63789403, compound

Product 1

HCID 974781-(4-Chlorophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Trifluoroacetic acid (3 mL) was added dropwise with stiffing at 0° C. to a solution of t-butyl 4-(4-chlorophenyl)piperazine-1-carboxylate (360.6 mg, 1.21 mmol, 1.00 equiv) in dichloromethane (12 mL). The resulting solution was stirred for 3 h at 20° C. in an oil bath. The pH value of the solution was adjusted to 7-8 with a saturated solution of sodium bicarbonate. The resulting solution was extracted with 6×20 mL of dichloromethane, the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 264.5 mg (102%) of 1-(4-chlorophenyl)piperazine as a yellow solid.

Workup

  1. extractionThe resulting solution was extracted with 6×20 mL of dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThis resulted in 264.5 mg (102%) of 1-(4-chlorophenyl)piperazine as a yellow solid

Sources & evidence

ORD record
ord-894e987ae71c455cb2343457a1f72ac0
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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