Benzyl 3-[(4-cyclobutylpiperazin-1-yl)carbonyl]azetidine-1-carboxylate → 1-(Azetidin-3-ylcarbonyl)-4-cyclobutylpiperazine

HRID 1402762Notes

Reaction equation

HRID 1402762 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]([CH:13]3[CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[CH2:14]3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[NH:15]1[CH2:14][CH:13]([C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[CH2:6][CH2:7]2)=[O:12])[CH2:16]1

Participants

4

Reactant 1

HCID 66739735Benzyl 3-[(4-cyclobutylpiperazin-1-yl)carbonyl]azetidine-1-carboxylate

Product 1

HCID 667393151-(Azetidin-3-ylcarbonyl)-4-cyclobutylpiperazineYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of benzyl 3-[(4-cyclobutylpiperazin-1-yl)carbonyl]azetidine-1-carboxylate (130 mg, 0.36 mmol) in EtOH (10 mL) was added 10% Pd/C (13 mg, 10% wt/wt). The flask was evacuated and the vacuum purged with N2 gas. The flask was evacuated again and the vacuum purged with H2 gas. After 16 hours the reaction mixture was filtered through Celite® and charged with 10% Pd/C (13 mg, 10% wt/wt). The flask was evacuated and the vacuum purged with N2 gas. The flask was evacuated again and the vacuum purged with H2 gas. After 23 hours, the reaction mixture was filtered through Celite® and the filtrate concentrated at reduced pressure to give the final compound (60 mg, 74%) which was used without further purification.

Workup

  1. customThe flask was evacuated
  2. customthe vacuum purged with N2 gas
  3. customThe flask was evacuated again
  4. customthe vacuum purged with H2 gas
  5. filtrationAfter 16 hours the reaction mixture was filtered through Celite®
  6. additioncharged with 10% Pd/C (13 mg, 10% wt/wt)
  7. customThe flask was evacuated
  8. customthe vacuum purged with N2 gas
  9. customThe flask was evacuated again
  10. customthe vacuum purged with H2 gas
  11. filtrationthe reaction mixture was filtered through Celite®
  12. concentrationthe filtrate concentrated at reduced pressure

Sources & evidence

ORD record
ord-006811dfd83144d2a5bc891c8af923eb
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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