Hydrochloric Acid → HCID 68575635, compound

HRID 656466Notes

Reaction equation

HRID 656466 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]23)[CH2:9]1)C1C=CC=CC=1.Cl.[H][H]>CO.[Pd]>[NH:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]23)[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68575735HCID 68575735, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68575635HCID 68575635, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.00 mmol of 1′-benzyl-6,7-dihydro-5H-spiro[imidazo[1,5-a]pyridine-8,3′-pyrrolidine] in 5 ml of methanol is admixed with 1 mmol of 2M aqueous hydrochloric acid and 0.10 g of 10% Pd/C. The reaction mixture is hydrogenated with 1 bar of hydrogen at 22° C. for 18 hours. The reaction mixture is filtered over Hyflo and the filtrate is evaporated. The residue is taken up in ethyl acetate and the amine is liberated with saturated aqueous sodium carbonate solution. The phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.

Workup

  1. filtrationThe reaction mixture is filtered over Hyflo
  2. customthe filtrate is evaporated
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-2cc918a4c8744859b92f65bef6598269
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

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