Hydrochloric Acid → (S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine

HRID 1784686Notes

Reaction equation

HRID 1784686 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C@@H:9]1[C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH3:28])=[CH:23][CH:22]=1)=O)(C)(C)C.Cl>ClCCl.C(OCC)(=O)C>[CH:29]1([N:27]([C:24]2[CH:25]=[CH:26][C:21]([C@H:9]3[CH2:10][NH:11][CH2:12][CH2:13][NH:8]3)=[CH:22][CH:23]=2)[CH3:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67117409(S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine

Product 1

HCID 67117423(S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazineYield 8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine in dichloromethane (4 mL) was added 4 N hydrogen chloride in ethyl acetate (4 mL). After stirring for 40 min, the white precipitate was collected, which included impurities. The mixture was purified by a reverse phase chromatography eluting 0.05% TFA in water-acetonitrile to afford (S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine (59 mg 8% in 2 steps) as a clear oil.

Workup

  1. customthe white precipitate was collected
  2. customThe mixture was purified by a reverse phase chromatography
  3. washeluting 0.05% TFA in water-acetonitrile

Sources & evidence

ORD record
ord-3d2e7a374b4a42c0bbc119a338b74a4c
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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