Benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylate → 1-(Azetidin-3-yl)-4-methylpiperazine

HRID 921642Notes

Reaction equation

HRID 921642 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[CH2:9]2)[CH2:4][CH2:3]1>CO.[Pd]>[NH:10]1[CH2:11][CH:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH2:9]1

Participants

4

Reactant 1

HCID 86708494Benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylate

Product 1

HCID 206598001-(Azetidin-3-yl)-4-methylpiperazineYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylate (1.45 g, 5.01 mmol) and Pd/C (0.320 g, 0.150 mmol) in methanol (30 mL) was hydrogenated at 30 psi over the weekend. The reaction mixture was filtered through celite and the filtrate was concentrated. The crude product 1-(azetidin-3-yl)-4-methylpiperazine (0.78 g, 5.02 mmol, 100% yield) was obtained as colorless oil and used without purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a635ec9e7d954fdb96254ca6fa06cd72
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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