Hydrochloric Acid → 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone hydrochloride

HRID 409587Notes

Reaction equation

HRID 409587 reaction equation
[C:1]1([C@H:11]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][S:27]([CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([N:38]5[CH2:42][CH2:41][C@H:40]([NH:43][C@@H:44]([C:46]6[C:55]7[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=7)[CH:49]=[CH:48][CH:47]=6)[CH3:45])[CH2:39]5)=[CH:34][CH:33]=4)(=[O:29])=[O:28])=[CH:21][CH:20]=3)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:56]>C(OCC)(=O)C.C(Cl)(Cl)Cl.O1CCOCC1>[ClH:56].[C:46]1([C@H:44]([NH:43][C@H:40]2[CH2:41][CH2:42][N:38]([C:35]3[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][S:27]([CH2:26][CH2:25][C:22]4[CH:23]=[CH:24][C:19]([N:16]5[CH2:17][CH2:18][C@H:14]([NH:13][C@@H:11]([C:1]6[C:10]7[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=7)[CH:4]=[CH:3][CH:2]=6)[CH3:12])[CH2:15]5)=[CH:20][CH:21]=4)(=[O:28])=[O:29])=[CH:33][CH:34]=3)[CH2:39]2)[CH3:45])[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 674070244-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone

Product 1

HCID 674090794-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone hydrochloride

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixed solvent comprising 2 ml of ethyl acetate and 1 ml of chloroform was dissolved 132.5 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone, 0.8 ml of a solution of 4N hydrogen chloride in dioxane was added thereto, and the precipitated solids were filtered and dried. This was recrystallized from ethanol to obtain 40.0 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]phenylethylsulfone hydrochloride (the following Table X, Example 12.017).

Workup

  1. additionwas added
  2. filtrationthe precipitated solids were filtered
  3. customdried
  4. customThis was recrystallized from ethanol

Sources & evidence

ORD record
ord-22288782261d498d8967719b7bfcbc69
Source dataset
uspto-grants-2014_06
Patent number
US08759387B2

Reaction notes

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