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

HRID 2068152Notes

Reaction equation

HRID 2068152 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-75d00748175244c2907862e1d211acb5
Source dataset
uspto-grants-2012_10
Patent number
US08293913B2

Reaction notes

Loading…