Hydrazine → 2-(3-Piperidinomethylthiophenoxy)ethylamine

HRID 464137Notes

Reaction equation

HRID 464137 reaction equation
NN.Br.[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=2)[S:14][CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3C2=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C(O)C>[N:4]1([CH2:10][C:11]2[CH:12]=[C:13]([CH:28]=[CH:29][CH:30]=2)[S:14][CH2:15][CH2:16][NH2:17])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 13505509N-{2-[3-(piperidinomethyl)thiophenoxy]ethyl}phthalimide hydrobromide

Product 1

HCID 135188252-(3-Piperidinomethylthiophenoxy)ethylamineYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Anhydrous hydrazine (1.79 g, 56.0 mmoles) was added to a suspension of N-{2-[3-(piperidinomethyl)thiophenoxy]ethyl}phthalimide hydrobromide (5.17 g, 11.2 mmoles) [prepared in Step D] in 200 mL of 95% ethanol, stirred at ambient temperature for 18 hours and filtered. The filtrate was stripped and the semi-solid residue was stirred with several portions of ether. Evaporation of the solvent gave 2.8 g of title compound as a yellow oil.

Workup

  1. filtrationfiltered
  2. stirringthe semi-solid residue was stirred with several portions of ether
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bddbc526da76424f8aa12ce4bcbad5eb
Source dataset
uspto-grants-1985_10
Patent number
US04546188

Reaction notes

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