Hydrazine hydrate (1:1) → 2-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-ethylamine

HRID 854608Notes

Reaction equation

HRID 854608 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 17978975HCID 17978975, compound

Product 1

HCID 179789732-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-ethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-{2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dione (0.087 g, 0.24 mmol) in ethanol (20 ml) is treated with hydrazine hydrate (1.0 ml, 2 mmol) and heated under reflux for 1.5 hours. Most of the solvent is evaporated and the resultant solution is ice cooled for 0.5 hours. The precipitate is filtered off and the filtrate is evaporated to afford 2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethylamine which is used directly, without further characterisation, in the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. customMost of the solvent is evaporated
  4. temperaturecooled for 0.5 hours
  5. filtrationThe precipitate is filtered off
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-a3a1ab9f59dd490484b4ef06967d42d7
Source dataset
uspto-grants-2007_08
Patent number
US07259173B2

Reaction notes

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