Hydrazine hydrate (1:1) → (2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)amine

HRID 1363015Notes

Reaction equation

HRID 1363015 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].O.NN>C(O)C>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH2:24])[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 669219102-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)-1H-isoindole-1,3(2H)-dione2×

Product 1

HCID 66921930(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)amineYield 104.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)-1H-isoindole-1,3(2H)-dione (for example, as prepared for Intermediate 30) (2.76 g, 6.03 mmol) was stirred under nitrogen in ethanol (40 ml) containing hydrazine monohydrate (commercially available, for example, from Aldrich) (0.71 ml, 15.1 mmol) at 80° C. for 2 h. The reaction was cooled with ice-water and filtered. The filter-cake was leached with ethanol and the combined filtrates were evaporated to an oil containing a white solid. This solid was mixed with DCM (about 20 ml) and filtered. The filter-cake was leached with more DCM and the combined filtrates were evaporated to give the title compound (2.07 g) as an oil: LCMS RT=2.32 min, ES+ve m/z 328 [M+H]+.

Workup

  1. filtrationfiltered
  2. customthe combined filtrates were evaporated to an oil
  3. additioncontaining a white solid
  4. additionThis solid was mixed with DCM (about 20 ml)
  5. filtrationfiltered
  6. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-c24c0c8d4ed4430ea70743a4ad6107db
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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