Hydrochloric Acid → (S)-1-(1-Methylpiperidin-4-yl)-4-(3-(pyrrolidin-2-yl)propylsulfonyl)piperazine hydrochloride

HRID 1643455Notes

Reaction equation

HRID 1643455 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH2:20][C@@H:21]3[CH2:25][CH2:24][CH2:23][N:22]3C(OC(C)(C)C)=O)(=[O:17])=[O:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.C(OCC)(=O)C.C(OCC)C>CO>[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH2:20][C@@H:21]3[CH2:25][CH2:24][CH2:23][NH:22]3)(=[O:17])=[O:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 59367787(S)-tert-Butyl 2-(3-(4-(1-methylpiperidin-4-yl)piperazin-1-ylsulfonyl)propyl)pyrrolidine-1-carboxylate

Product 1

HCID 66755244(S)-1-(1-Methylpiperidin-4-yl)-4-(3-(pyrrolidin-2-yl)propylsulfonyl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen chloride in methanol (5 ml, 1.25 mol/l) was added to (S)-tert-butyl 2-(3-(4-(1-methylpiperidin-4-yl)piperazin-1-ylsulfonyl)propyl)pyrrolidine-1-carboxylate (0.27 g, 0.589 mmol) and the mixture was refluxed. After 1 h ethyl acetate (10 ml) and diethyl ether (20 ml) were added to the suspension, the mixture was stirred in an ice bath for 1 h and the precipitate was filtered out with suction, washed with diethyl ether and dried in vacuo. Yield: 0.22 g (79%)

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationthe precipitate was filtered out with suction
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-aee9bdf88e7d435b920f7160c7772910
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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