1,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate → 1-{4-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}piperazine

HRID 419406Notes

Reaction equation

HRID 419406 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 1

HCID 594529421,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate

Product 1

HCID 594526001-{4-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}piperazineYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1,1-dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate (0.75 g, 1.80 mmol, combined batches) was stirred at rt under N2 in 20% TFA in DCM (40 mL) for approximately 2 h. The solution was then concentrated under vacuum. The residue was dissolved in DCM and aqueous (saturated) NaHCO3. The aqueous layer was separated and extracted with DCM (3×). The combined organic layers were dried over MgSO4, filtered, then concentrated and purified by silica gel chromatography to give the title compound of step F (446 mg, 1.40 mmol, 78%) as a light tan solid. MS (ESI): 318 [M+H]+.

Workup

  1. concentrationThe solution was then concentrated under vacuum
  2. dissolutionThe residue was dissolved in DCM
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (3×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-834ffd9cb7f74bd2bd75336d7465ee5f
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…