Hydrazine hydrate (1:1) → HCID 22380629, compound

HRID 895624Notes

Reaction equation

HRID 895624 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][N:22]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22380593HCID 22380593, compound

Product 1

HCID 22380629HCID 22380629, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Subsequently, the resulting crude 1-(tert-butoxycarbonyl)-4-[(2-phthalimidylmethylphenyl)amino]piperidine (420 mg) was dissolved in ethanol (8 ml), added with hydrazine monohydrate (0.23 ml) and stirred at room temperature for 1 hour and at 40° C. for 1 hour. After insoluble matters were removed by filtration from the reaction mixture, the solvent was evaporated under reduced pressure. The residue was added with water (10 ml) and extracted twice with dichloromethane (10 ml). The solvent was evaporated under reduced pressure to obtain 219 mg of 1-(tert-butoxycarbonyl)-4-[(2-aminomethylphenyl)amino]piperidine.

Workup

  1. customAfter insoluble matters were removed by filtration from the reaction mixture
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with water (10 ml)
  4. extractionextracted twice with dichloromethane (10 ml)
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-65fe43c19ccb401b87f41623f3dbba7d
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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