Hydrochloric Acid → HCID 67408461, compound

HRID 409591Notes

Reaction equation

HRID 409591 reaction equation
[CH3:1][N:2]([CH3:25])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[ClH:26]>C(OCC)(=O)C>[ClH:26].[ClH:26].[NH2:17][C@H:14]1[CH2:15][CH2:16][N:12]([C:9]2[CH:8]=[CH:7][C:6]([S:3]([N:2]([CH3:25])[CH3:1])(=[O:4])=[O:5])=[CH:11][CH:10]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68236280HCID 68236280, compound

Product 1

HCID 67408461HCID 67408461, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In ethyl acetate was dissolved 8.39 g of tert-butyl [(S)-1-(4-dimethylsulfamoylphenyl)-pyrrolidin-3-yl]carbamate, 200 ml of a solution of 4M hydrochloric acid in ethyl acetate was added thereto, and the mixture was stirred at room temperature for 3 days. The solvent was evaporated, and then, diethyl ether was added to the residue, and the precipitates were collected by filtration to obtain 4-[(S)-3-aminopyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide dihydrochloride. To the 4-[(S)-3-aminopyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide dihydrochloride were added a saturated aqueous sodium bicarbonate solution and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated under reduced pressure to obtain 5.85 g of 4-[(S)-3-aminopyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. additiondiethyl ether was added to the residue
  4. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-6e1fa31fc71f4ab2b56d7f096a2e9e91
Source dataset
uspto-grants-2014_06
Patent number
US08759387B2

Reaction notes

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