1,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylate → (2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride

HRID 43366

Reaction equation

HRID 43366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@@H:12]2[CH3:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]2[CH3:24])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 582844531,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylate

Product 1

HCID 67028562(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylate (may be prepared as described in Description 3) (crude weight 24.14 g, theoretical 49.9 mmol) was suspended in 4M HCl in 1,4-dioxane (80 mL, excess) and stirred vigorously for 3 hours. The sample was evaporated, suspended in diethyl ether (100 mL) and filtered through a sinter. The collected solid was dried under vacuum at 40° C. for 18 hours to yield the title compound as a yellow solid (15.45 g).

Workup

  1. customThe sample was evaporated
  2. filtrationfiltered through a sinter
  3. customThe collected solid was dried under vacuum at 40° C. for 18 hours

Sources & evidence

ORD record
ord-89c011896b28485989af24d645625973
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Linked notes

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