1,1-Dimethylethyl 4-[[2-methoxy-5-(1-methylethyl)phenyl]methyl]-1-piperazinecarboxylate → 1-[[2-Methoxy-5-(1-methylethyl)phenyl]methyl]-piperazine

HRID 38291Notes

Reaction equation

HRID 38291 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:11])[CH3:10])=[CH:5][C:4]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1>C(O)(C(F)(F)F)=O.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:11])[CH3:10])=[CH:5][C:4]=1[CH2:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 671315531,1-Dimethylethyl 4-[[2-methoxy-5-(1-methylethyl)phenyl]methyl]-1-piperazinecarboxylate

Product 1

HCID 39064451-[[2-Methoxy-5-(1-methylethyl)phenyl]methyl]-piperazineYield 126.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from step (a) (1.98 g) in TFA (4 ml) and dichloromethane (2 ml) was stirred for 2 h. The solvent was removed in vacuo and the residue azeotroped with toluene. Aq. potassium carbonate was added and the mixture was extracted with dichloromethane. The organic extracts were dried (MgSO4) and evaporated in vacuo to give the sub-title compound (1.79 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with toluene
  3. additionAq. potassium carbonate was added
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb22901767bf426b84b966e953a02f2d
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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