Hydrochloric Acid → HCID 67392333, compound

HRID 2067960Notes

Reaction equation

HRID 2067960 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=1)[CH2:9][CH2:10][CH3:11])(C)(C)C.[ClH:23].O1CCOCC1>ClCCl>[ClH:23].[ClH:23].[CH3:21][S:18]([C:16]1[CH:17]=[C:12]([CH:8]([NH2:7])[CH2:9][CH2:10][CH3:11])[CH:13]=[N:14][CH:15]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58443386HCID 58443386, compound

Product 1

HCID 67392333HCID 67392333, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of [1-(5-methanesulfonyl-pyridin-3-yl)-butyl]-carbamic acid tert-butyl ester (3.2 g, 9.6 mmol) in dichloromethane (12 mL) is treated HCl in dioxane (4.0 N, 24 mL, 96 mmol) and stirred for 30 min. The solvent is then removed in vacuo. The resultant residue is triturated with anhydrous ethyl ether (50 mL) and filtered (note: the collected solids are hygroscopic and turn into a liquid when left exposed to air.) Methanol is added and the solution is concentrated in vacuo to yield 1-(5-methanesulfonyl-pyridin-3-yl)-butylamine dihydrochloride (2.8 g, 100%) as a dark brown solid.

Workup

  1. customThe solvent is then removed in vacuo
  2. customThe resultant residue is triturated with anhydrous ethyl ether (50 mL)
  3. filtrationfiltered (note
  4. waitleft
  5. addition) Methanol is added
  6. concentrationthe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-02a10f2e95cb4dd8a0d79746aaeed1dd
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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