Hydrazine hydrate (1:1) → 3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine
Reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[O:11][CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>CO>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 16.3 g of the N-[3-[3-(piperidinomethyl)phenoxy]propyl]phthalimide in 150 ml of methanol was added 2.3 g of hydrazine monohydrate, and the mixture was heated at 70° C. for 4 hours. The mixture was cooled, then the solvent was distilled off, 30 ml of 6N hydrochloric acid was added to the residue, and the mixture was heated at 60° C. for 15 minutes. The resulting mixture was cooled, the insolubles were then filtered off, the solution was made alkaline with potassium hydroxide and subjected to extraction with a mixture of ethyl acetate and diethyl ether (1:1), and the organic layer was dried over magnesium sulfate and thereafter distilled to remove the solvent, giving 8.3 g of pale yellow oily 3-[3-(1-piperidinomethyl)phenoxy]propylamine (yield 78% ).
Workup
- temperatureThe mixture was cooled
- distillationthe solvent was distilled off
- addition30 ml of 6N hydrochloric acid was added to the residue
- temperaturethe mixture was heated at 60° C. for 15 minutes
- temperatureThe resulting mixture was cooled
- filtrationthe insolubles were then filtered off
- extractionsubjected to extraction with a mixture of ethyl acetate and diethyl ether (1:1)
- dry with materialthe organic layer was dried over magnesium sulfate
- distillationdistilled
- customto remove the solvent
Sources & evidence
- ORD record
- ord-9a144552368646b29bf16aa0e1e8441b
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401739
Reaction notes
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