Hydrazine → 2-(4-Aminomethyl-4-fluoro-piperidin-1-ylmethyl)-4,6-dichlorophenol

HRID 2112556Notes

Reaction equation

HRID 2112556 reaction equation
NN.[Cl:3][C:4]1[C:5]([OH:31])=[C:6]([CH:27]=[C:28]([Cl:30])[CH:29]=1)[CH2:7][N:8]1[CH2:13][CH2:12][C:11]([CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)([F:14])[CH2:10][CH2:9]1>C(O)C>[NH2:16][CH2:15][C:11]1([F:14])[CH2:12][CH2:13][N:8]([CH2:7][C:6]2[CH:27]=[C:28]([Cl:30])[CH:29]=[C:4]([Cl:3])[C:5]=2[OH:31])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 690694182-[1-(3,5-Dichloro-2-hydroxy-benzyl)-4-fluoro-piperidin-4-ylmethyl]-isoindole-1,3-dione

Product 1

HCID 230692642-(4-Aminomethyl-4-fluoro-piperidin-1-ylmethyl)-4,6-dichlorophenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine (10 ml) was added to a solution of 2-[1-(3,5-dichloro-2-hydroxy-benzyl)-4-fluoro-piperidin-4-ylmethyl]-isoindole-1,3-dione (20.7 g) in ethanol (600 ml). The obtained solution was stirred for 5 hours while heating to reflux, and then subjected to heated filtration. The filtrate was concentrated, water was added to the residue, and then extraction with dichloromethane was followed by concentration. The obtained residue was recrystallized from isopropyl ether-pentane to obtain 2-(4-aminomethyl-4-fluoro-piperidin-1-ylmethyl)-4,6-dichlorophenol.

Workup

  1. temperaturewhile heating
  2. temperatureto reflux
  3. temperatureto heated
  4. filtrationfiltration
  5. concentrationThe filtrate was concentrated
  6. additionwater was added to the residue
  7. extractionextraction with dichloromethane
  8. concentrationwas followed by concentration
  9. customThe obtained residue was recrystallized from isopropyl ether-pentane

Sources & evidence

ORD record
ord-a60542660a33494fba249a1c7dac629b
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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