Hydrazine hydrate (1:1) → 1-Amino-3-(2-bromophenyl)piperidin-2-one

HRID 2235796Notes

Reaction equation

HRID 2235796 reaction equation
O.[NH2:2][NH2:3].[Br:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([CH2:16][CH2:17][CH2:18]Cl)[C:12](OC)=[O:13]>C(O)C>[NH2:2][N:3]1[CH2:18][CH2:17][CH2:16][CH:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[Br:4])[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 67067456Methyl 2-(2-bromophenyl)-5-chloropentanoate

Product 1

HCID 668389981-Amino-3-(2-bromophenyl)piperidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-bromophenylacetate (2.0 g) in DMF (5 mL) was added to a suspension of sodium hydride (containing mineral oil at 40%, 384 mg) in DMF (20 mL) under ice-cooling. The reaction solution was stirred for 10 minutes, further stirred at room temperature for 30 minutes and then ice-cooled again. A solution of 1-chloro-3-iodopropane (1.96 g) in DMF (5 mL) was added to the reaction mixture, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of methyl 2-(2-bromophenyl)-5-chloropentanoate. Hydrazine monohydrate (4 mL) was added to a solution of the resulting crude methyl 2-(2-bromophenyl)-5-chloropentanoate (2.895 g) in ethanol (20 mL), and the reaction solution was stirred at room temperature for three hours. Hydrazine monohydrate (8 mL) was further added to the reaction solution, and the reaction solution was stirred at room temperature for two days. The reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate and were added to the residue, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 1.504 g of the crude purified title compound. The property value of the compound is as follows.

Workup

  1. stirringthe reaction solution was stirred at room temperature for two days
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionSaturated sodium bicarbonate water and ethyl acetate and were added to the residue
  4. customthe organic layer was separated
  5. washThe resulting organic layer washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain 1.504 g of the crude
  9. custompurified title compound

Sources & evidence

ORD record
ord-830eea57090c4ddd8639815490edabe3
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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