Hydrochloric Acid → (S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazine tetrahydrochloride

HRID 1784682Notes

Reaction equation

HRID 1784682 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]2[CH2:31][CH2:30][C@H:29]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:28]2)=[CH:23][CH:22]=1)=O)(C)(C)C.[ClH:37]>ClCCl.C(OCC)(=O)C>[ClH:37].[ClH:37].[ClH:37].[ClH:37].[N:32]1([C@H:29]2[CH2:30][CH2:31][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C@H:9]4[CH2:10][NH:11][CH2:12][CH2:13][NH:8]4)=[CH:26][CH:25]=3)[CH2:28]2)[CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67117414(S)-1,4-di(t-butoxycarbonyl)-2-(4-((S)-3-(pyrrolidin-1-yl) pyrrolidin-1-yl)phenyl)piperazine

Product 1

HCID 67117390(S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazine tetrahydrochlorideYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-((S)-3-(pyrrolidin-1-yl) pyrrolidin-1-yl)phenyl)piperazine (479 mg, 0.957 mmol) in dichloromethane (4 mL) was added 4 N hydrogen chloride in ethyl acetate (4 mL) at room temperature. After stirring for 3 h, the resulting precipitate was collected and dried in vacuo to afford (S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl)piperazine tetrahydrochloride (370 mg, 87%) as a white solid.

Workup

  1. customthe resulting precipitate was collected
  2. customdried in vacuo

Sources & evidence

ORD record
ord-272d8969cbd642f9a3d2a4c56e57bbf6
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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