HCID 21618684, compound → tert-Butyl 2-methylpiperazine-1-carboxylate

HRID 874937Notes

Reaction equation

HRID 874937 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CO>[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19]

Participants

3

Reactant 1

HCID 21618684HCID 21618684, compound

Product 1

HCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateYield 116.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Benzyl 1-tert-butyl 2-methylpiperazine-1,4-dicarboxylate (3.0 g, 8.97 mmol) was dissolved in MeOH (30 mL) and purged with nitrogen for 5 min. 10% palladium on charcoal (300 mg) was added, and the reaction mixture was hydrogenated at room temperature for 2 h. The mixture was then filtered through Celite and the clear filtrate was concentrated under reduced pressure to obtain tert-butyl 2-methylpiperazine-1-carboxylate (2.1 g, crude), which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 4.23-4.15 (m, 1H), 3.82-3.77 (m, 1H), 3.01-2.88 (m, 3H), 2.78-2.75 (m, 1H), 2.71-2.63 (m, 1H), 1.47 (s, 9H), 1.22-1.21 (m, 3H). MS (ESI) m/z: Calculated for C10H20N2O2: 200.15. found: 201.0 (M+H)+

Workup

  1. custompurged with nitrogen for 5 min
  2. addition10% palladium on charcoal (300 mg) was added
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe clear filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30fd45fb94e24a2bb2fbee78a029e971
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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