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

HRID 370546Notes

Reaction equation

HRID 370546 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-a549ccd604f0460b9f545ad79db30cc9
Source dataset
uspto-grants-1985_07
Patent number
US04526973

Reaction notes

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