1-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine → 1-[[(6Rs)-6-aminomethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride

HRID 352937Notes

Reaction equation

HRID 352937 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[C:36]([Cl:41])[CH:37]=5)[CH:32]=4)(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[O:21])[CH:14]=[CH:13][C:12]=2[CH2:11]1)=O)(C)(C)C>Cl.C(O)C>[ClH:41].[NH2:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([C:20]([N:22]3[CH2:23][CH2:24][N:25]([S:28]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[C:36]([Cl:41])[CH:37]=5)[CH:32]=4)(=[O:29])=[O:30])[CH2:26][CH2:27]3)=[O:21])[CH:14]=[CH:13][C:12]=2[CH2:11]1

Participants

4

Reactant 1

HCID 227109191-[[(6RS)-6-(N-tert-Butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

Product 1

HCID 227103521-[[(6Rs)-6-aminomethyl-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

In saturated aqueous hydrochloric acid in ethanol (5 ml), 1-[[(6RS)-6-(N-tert-butoxycarbonylaminomethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine (0.22 g) was dissolved, followed by stirring at room temperature for 90 minutes. The residue obtained by distilling off the solvent under reduced pressure was recrystallized from a mixed solvent of ethanol and diethyl ether, whereby the title compound (0.14 g, 68%) was obtained.

Workup

  1. customThe residue obtained
  2. distillationby distilling off the solvent under reduced pressure
  3. customwas recrystallized from a mixed solvent of ethanol and diethyl ether, whereby the title compound (0.14 g, 68%)
  4. customwas obtained

Sources & evidence

ORD record
ord-4529de2df39747948598f91998ee2dcd
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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