Hydrochloric Acid → 5-benzyloctahydro-1H-pyrrolo[3,4-c]pyridine-2,5-diium chloride

HRID 2092211Notes

Reaction equation

HRID 2092211 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]2[CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:24].C(OCC)C>C(O)C.C(O)(C)C>[Cl-:24].[CH2:1]([NH+:8]1[CH2:13][CH2:12][CH:11]2[CH2:14][NH2+:15][CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68725101tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

Product 1

HCID 866476885-benzyloctahydro-1H-pyrrolo[3,4-c]pyridine-2,5-diium chloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

1.355 g of tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (4.28 mmol) were dissolved in 10 ml of ethanol. To the solution 20 ml of 5 N HCl in isopropanol were added and the obtained mixture was stirred at room temperature for 16 h. After addition of diethyl ether the product precipitated. The product was filtered and after an additional washing with diethyl ether, the product was dried. Additional product was obtained by concentration of the filtrates and crystallization from diethyl ether. Combined amounts of product were 1.07 g.

Workup

  1. customprecipitated
  2. filtrationThe product was filtered
  3. washafter an additional washing with diethyl ether
  4. customthe product was dried
  5. customAdditional product was obtained by concentration of the filtrates and crystallization from diethyl ether

Sources & evidence

ORD record
ord-880c6940d7a44c1bb8358e884d191516
Source dataset
uspto-grants-2013_05
Patent number
US08440694B2

Reaction notes

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