Hydrazine hydrate (1:1) → HCID 13505514, compound

HRID 1719214Notes

Reaction equation

HRID 1719214 reaction equation
Br.[N:2]1([CH2:8][C:9]2[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=2)[S:12][CH2:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.NN>C(O)C.CCOCC>[N:2]1([CH2:8][C:9]2[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=2)[S:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13505513HCID 13505513, compound

Product 1

HCID 13505514HCID 13505514, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-{3-[3-(piperidinomethyl)thiophenoxy]propyl}phthalimide hydrobromide (58.0 g, 0.12 mole) [prepared in Step A] in 1650 mL of 95% ethanol was added hydrazine hydrate (26.9 g, 0.54 mole) and the reaction mixture was heated at 45° for 4.5 hours. The mixture was diluted with 500 mL of ether, filtered and the filtrate evaporated to dryness to give the title compound as an amber oil (14.1 g). An aliquot was distilled to a colorless oil, b.p. 154°-155°/0.15 mm Hg.

Workup

  1. temperaturethe reaction mixture was heated at 45° for 4.5 hours
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-716e48125727491da7a17dab4e0e937e
Source dataset
uspto-grants-1985_09
Patent number
US04539316

Reaction notes

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