Benzyl 4-{1-[(methylamino)carbonyl]pyrrolidin-3-yl}piperazine-1-carboxylate → N-methyl-3-piperazin-1-ylpyrrolidine-1-carboxamide

HRID 1241419Notes

Reaction equation

HRID 1241419 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][N:13](C(OCC3C=CC=CC=3)=O)[CH2:12][CH2:11]2)[CH2:6]1)=[O:4]>C(O)C.[Pd]>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 21934712Benzyl 4-{1-[(methylamino)carbonyl]pyrrolidin-3-yl}piperazine-1-carboxylate

Product 1

HCID 21934633N-methyl-3-piperazin-1-ylpyrrolidine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

45-4 (0.10 g, 0.30 mmol) was dissolved in 10 mL of absolute ethanol. To this solution was added 10% Pd/C catalyst. This was then hydrogenolyzed for 7 hours at 60 psi. The catalyst was then filtered off and the filtrate was evaporated to an oil and flushed with methanol to afford 45-5. 1H-NMR (CD3OD): 3.62(m, 2H); 3.49(m, 2H); 3.24(t, 4H); 3.14(m, 1H); 3.03(m, 1H); 2.82(m, 2H); 2.72(complex, 4H); 2.20(m, 1H); 1.86(m, 1H).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate was evaporated to an oil
  3. customflushed with methanol
  4. customto afford 45-5

Sources & evidence

ORD record
ord-bb01c045d75446d5a7d3f7d62f3e7ecb
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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