N,N-Diethyl-2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetamide → N,N-diethyl-7-amino-1,2,3,4-tetrahydroisoquinolin-1-acetamide dihydrochloride

HRID 369968Notes

Reaction equation

HRID 369968 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4](=[O:29])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8][N:7]1C(OCC1C=CC=CC=1)=O)[CH3:2].[ClH:32].CO>CO.[Pd]>[ClH:32].[ClH:32].[CH2:30]([N:3]([CH2:1][CH3:2])[C:4](=[O:29])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8][NH:7]1)[CH3:31]

Participants

5

Reactant 2

HCID 21584373N,N-Diethyl-2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetamideHCID 21893726Hydrochloride methanol

Product 1

HCID 21584358N,N-diethyl-7-amino-1,2,3,4-tetrahydroisoquinolin-1-acetamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a pressure bottle charged with N,N-diethyl-2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetamide (10 mmols) dissolved in methanol (150 ml) and saturated methanol-HCl (20 ml) was added 10% Pd-C (250 mg), and the reaction was hydrogenated for 1 h. The catalyst was removed by filtration and the solvent evaporated to yield N,N-diethyl-7-amino-1,2,3,4-tetrahydroisoquinolin-1-acetamide dihydrochloride which was used as such in the next step.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-4a1a0477a9e04ded8cc2ff1ac02d6237
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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