Dichloromethane → 1-(3-Chlorophenyl)piperazine

HRID 1405435Notes

Reaction equation

HRID 1405435 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[Cl:27]CCl>FC(F)(F)C(O)=O>[Cl:27][C:4]1[CH:5]=[C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:7]=[CH:8][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 10935225185460-26-8

Product 1

HCID 13551-(3-Chlorophenyl)piperazineYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of t-butyl 4-(4-methoxyphenyl)piperazine-1-carboxylate (1.3 g, 4.39 mmol, 1.00 equiv) in dichloromethane (11 mL) and trifluoroacetic acid (6 mL) was placed in a 50-mL round bottom flask and stirred for 3 h at 20° C. in an oil bath. The solution was adjusted to a pH value of 7-8 with a saturated aqueous solution of sodium bicarbonate, and extracted with 6×15 mL of dichloromethane. The organic layers combined and dried over anhydrous sodium sulfate, filtered to remove solids, and concentrated under vacuum yielding 430 mg (50%) of 1-(3-chlorophenyl)piperazine as a yellow solid.

Workup

  1. extractionextracted with 6×15 mL of dichloromethane
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d0ac1a3959284372888db603c260d124
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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