Piperazine → Isobutyl piperazine-1-carboxylate

HRID 2085708Notes

Reaction equation

HRID 2085708 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9].[OH-].[Na+]>Cl>[N:1]1([C:8]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformate

Product 1

HCID 11788701Isobutyl piperazine-1-carboxylateYield 58,523%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of piperazine (8.61 g, 0.1 mmol) in 1M HCl (200 mL) at room temperature was treated with isobutyl chloroformate (13.66 g, 13 mL, 0.1 mol), adjusted to pH 3 with 1M NaOH over 1 to 2 hours, stirred for 18 hours, quenched with 4M KOH, and extracted with dichloromethane (2×100 mL). The combined extracts were dried (MgSO4), filtered, and concentrated to provide 10.9 g (59%) the desired product. MS (ESI(+)) m/e 187 (M+H)+.

Workup

  1. customquenched with 4M KOH
  2. extractionextracted with dichloromethane (2×100 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba13f2428f43447382a5976d9aa70b8b
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

Loading…