Hydrochloric Acid → HCID 22485589, compound

HRID 2181303Notes

Reaction equation

HRID 2181303 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][CH:11]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:12][CH2:13][N:14](CC1C=CC=CC=1)[CH3:15])C1C=CC=CC=1.Cl>CO.[Pd]>[CH3:1][NH:8][CH2:9][CH2:10][CH:11]([N:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)[CH2:12][CH2:13][NH:14][CH3:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22485500HCID 22485500, compound

Product 1

HCID 22485589HCID 22485589, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N,N′-dibenzyl-N,N′-dimethyl-3-(1-pyrrolidinyl)-1,5-pentanediamine (249.1 mg, 0.657 mmol) in methanol (3.0 mL) were added concentrated hydrochloric acid (0.33 mL, 4.0 mmol) and 10% palladium on charcoal (50.0 mg), and the mixture was stirred at 50° C. for 14 hours under hydrogen. Insoluble materials were removed by filtration through a membrane filter, and the filtrate was concentrated under reduced pressure. The residue was adsorbed on an alumina column, and eluted with methanol-chloroform (1:4). The eluate was concentrated under reduced pressure to afford the title compound as a colorless oil (101.9 mg, yield: 78%).

Workup

  1. customInsoluble materials were removed by filtration through a membrane
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluted with methanol-chloroform (1:4)
  5. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74aecd32e25341b2b37a4bde1fb732bd
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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