Trifluoroacetic acid → HCID 20232515, compound

HRID 2400763Notes

Reaction equation

HRID 2400763 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(N(CC)CC)C.[Cl:21][C:22]1[CH:31]=[CH:30][C:25]([CH:26]=[CH:27]CCl)=[CH:24][CH:23]=1.FC(F)(F)C(O)=O>CS(C)=O.ClCCl.O>[Cl:21][C:22]1[CH:31]=[CH:30][C:25](/[CH:26]=[CH:27]/[CH2:1][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 20232515HCID 20232515, compoundYield 106.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N—BOC-piperazine (4.3 g) and triethylamine (9 ml) in dimethylsulfoxide (40 ml) at 0° C. under nitrogen was treated with 4-chlorocinnamyl chloride (5 g) and the resulting solution was stirred at room temperature for 18 hours, poured into water, extracted with ethyl acetate (three times), dried over sodium sulfate and concentrated in vacuo. The residue was filtered over silica gel to afford crude 4-[(E)-3-(4-Chloro-phenyl)-allyl]-piperazine-1-carboxylic acid tert-butyl ester. This compound was dissolved in dichloromethane (30 ml) and treated with trifluoroacetic acid (10 ml) at room temperature for 18 hours. Concentration afforded 1-[(E)-3-(4-Chloro-phenyl)-allyl]-piperazine (5.8 g), which was characterised by its mass and NMR spectra. MS (ES+) 151/153 (M-piperazine), 237/239 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationThe residue was filtered over silica gel
  5. customto afford crude 4-[(E)-3-(4-Chloro-phenyl)-allyl]-piperazine-1-carboxylic acid tert-butyl ester
  6. concentrationConcentration

Sources & evidence

ORD record
ord-d821f718feeb404fb6a4a968964f5de1
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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