Hydrazine hydrate (1:1) → 6-(Methyloxy)-2-(1-propyl-4-piperidinyl)-1,2,3,4-tetrahydro-7-isoquinolinamine

HRID 1014311Notes

Reaction equation

HRID 1014311 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-])=O)[CH2:9][N:8]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]1)[CH2:7][CH2:6]2.O.NN>[Fe](Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[NH2:13])[CH2:9][N:8]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]1)[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 594416526-(Methyloxy)-7-nitro-2-(1-propyl-4-piperidinyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 594417696-(Methyloxy)-2-(1-propyl-4-piperidinyl)-1,2,3,4-tetrahydro-7-isoquinolinamineYield 42%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 6-(methyloxy)-7-nitro-2-(1-propyl-4-piperidinyl)-1,2,3,4-tetrahydroisoquinoline (1.43 g, 4.35 mmol), hydrazine hydrate (1.0 mL, 30.5 mmol), iron(III)chloride (0.180 g, 1.09 mmol), activated carbon (2 g), and methanol (50 mL) was maintained at 65° C. for 12 hours, cooled, and filtered through celite (rinsed with additional methanol). Filtrates were concentrated, redissolved in ethyl acetate, and washed twice with saturated aqueous sodium chloride and sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford 6-(methyloxy)-2-(1-propyl-4-piperidinyl)-1,2,3,4-tetrahydro-7-isoquinolinamine (0.550 g, 42%). 1H NMR (400 MHz, CDCl3) δ ppm 6.49 (s, 1 H), 6.37 (s, 1 H), 3.80 (s, 3 H), 3.64 (s, 4 H), 2.99-3.15 (m, 2 H), 2.70-2.85 (m, 4 H), 2.49 (s, 1 H), 2.33 (s, 2 H), 2.01 (s, 2 H), 1.89 (s, 2 H), 1.77 (s, 2 H), 1.56 (s, 2 H), 0.91 (t, J=7.33 H, 3 H).

Workup

  1. temperaturecooled
  2. filtrationfiltered through celite (rinsed with additional methanol)
  3. concentrationFiltrates were concentrated
  4. dissolutionredissolved in ethyl acetate
  5. washwashed twice with saturated aqueous sodium chloride and sodium bicarbonate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5bf26d3aa8a045ecad9337cc7dbfadf1
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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