HCID 21584287, compound → HCID 21584282, compound

HRID 369989Notes

Reaction equation

HRID 369989 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH:12]2[CH2:15][CH2:16][CH3:17])=[CH:7][CH:6]=1)([O-])=O>C(O)C.[Pd]>[ClH:1].[CH2:15]([CH:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([NH2:2])[CH:14]=2)[CH2:9][CH2:10][NH:11]1)[CH2:16][CH3:17]

Participants

4

Reactant 1

HCID 21584287HCID 21584287, compound

Product 1

HCID 21584282HCID 21584282, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 7-nitro-1-propyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.51 g, 9.78 mmol) in ethanol (150 ml) was added 10% Pd-C (0.3 g) and the reaction mixture was hydrogenated at 50 psi for 3 h. The solution was filtered and the filtrate was concentrated and absolute ethanol was added to help evaporate any excess water. The resulting solid was triturated with isopropanol (30 ml) to give the title compound (1.42 g , 64%) as an off-white solid, m.p. 192-4° C.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. additionabsolute ethanol was added
  4. customto help evaporate any excess water
  5. customThe resulting solid was triturated with isopropanol (30 ml)

Sources & evidence

ORD record
ord-d26d3bb66e784589961342251f3e6af9
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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