Hydrochloric Acid → HCID 66936209, compound

HRID 1366617Notes

Reaction equation

HRID 1366617 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5](CC2C=CC=CC=2)[CH2:4]1.[ClH:18]>CO.[Pd]>[ClH:18].[ClH:18].[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66936495HCID 66936495, compound

Product 1

HCID 66936209HCID 66936209, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the first eluting enantiomer of N,N,5,5-tetramethyl-1-(phenylmethyl)-3-pyrrolidinamine (1.0607 g, 4.569 mmol) in MeOH (40 mL) was added 1 N aq. HCl (9.1 mL, 9.1 mmol) and 10% Pd/C (50% water, 265 mg). The mixture was hydrogenated overnight and was then filtered through a 0.2 μm PTFE membrane. The solution was concentrated in vacuo, and the residue was azeotroped with MeOH (5×50 mL) to give crude N,N,5,5-tetramethyl-3-pyrrolidinamine dihydrochloride (1.0206 g, >100% crude yield) as a white foam. LCMS: (M+H)+: 143.1.

Workup

  1. filtrationwas then filtered through a 0.2 μm PTFE membrane
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was azeotroped with MeOH (5×50 mL)

Sources & evidence

ORD record
ord-a00c3b78635f49228d0d89706f14a1df
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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