HCID 54228801, compound → HCID 53885859, compound

HRID 1861795Notes

Reaction equation

HRID 1861795 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[CH:4][C:3]=1[N+:21]([O-])=O>CO.[Ni]>[NH2:21][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[NH2:1])[O:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1

Participants

4

Reactant 1

HCID 54228801HCID 54228801, compound

Product 1

HCID 53885859HCID 53885859, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[(4-amino-3-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline (250 mg, 0.8 mmol) and Raney Ni (about 200 mg) in MeOH (15 mL) was shaken under H2 (25 parr) for 4 h, then filtered. The filtrate was evapoated, and the residue was purified by chromatography over silica gel (CHCl3-EtOH-NH4OH, 60:40:0.5) to give 218 mg (96%) of N-[(3,4-diaminophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline as a brown viscous oil. 1H NMR (CDCl3): 2.87-2.96 (m, 10H), 3.764 (s, 2H), 4.122 (t, 2H, J=5), 6.545 (dd, 1H, J=8; 2), 6.362 (d, 1H, J=2), 6.633 (d, 1H, J=8), 7.01-7.20 (m, 5H).

Workup

  1. filtrationfiltered
  2. customthe residue was purified by chromatography over silica gel (CHCl3-EtOH-NH4OH, 60:40:0.5)

Sources & evidence

ORD record
ord-aeb8ad20f63c4510aee6e73c79c7b52a
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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