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

HRID 2164248Notes

Reaction equation

HRID 2164248 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-b0b95adbbdc64286b688f869726a370b
Source dataset
uspto-grants-1985_03
Patent number
US04503051

Reaction notes

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