Hydrazine hydrate (1:1) → HCID 15257492, compound

HRID 2051393Notes

Reaction equation

HRID 2051393 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH2:10][CH2:9]2)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15257494HCID 15257494, compound

Product 1

HCID 15257492HCID 15257492, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2-phthalimidoethyl)-4-(3-indolyl)piperidine (6.3 g) and hydrazine monohydrate (2.2 g) in ethanol (250 ml) was refluxed for 70 minutes. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was treated with 5% sodium hydroxide solution (300 ml) and extracted with ethyl acetate (300 ml). The organic layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The evaporation of solvent gave 1-(2-aminoethyl)-4-(3-indolyl)piperidine (3.74 g).

Workup

  1. temperaturewas refluxed for 70 minutes
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was treated with 5% sodium hydroxide solution (300 ml)
  6. extractionextracted with ethyl acetate (300 ml)
  7. washThe organic layer was washed with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe evaporation of solvent

Sources & evidence

ORD record
ord-76d616d7b4ce44fabd74e3e143d7ecd3
Source dataset
uspto-grants-1991_05
Patent number
US05017703

Reaction notes

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