Dichloromethane → tert-Butyl 4-isobutyrylpiperazine-1-carboxylate

HRID 538036Notes

Reaction equation

HRID 538036 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[C:17](Cl)(=[O:21])[CH:18]([CH3:20])[CH3:19]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 62325Isobutyryl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 60708297tert-Butyl 4-isobutyrylpiperazine-1-carboxylateYield 101.9%

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl-1-piperazinecarboxylate (5.0 g, 26.8 mmol) in DCM (100 mL) triethylamine (5.6 mL, 40.3 mmol) was added, the mixture was cooled down to 0° C. and isobutyryl chloride (4.2 mL, 40.3 mmol) was added. The reaction was allowed to warm up to room temperature and after 3 hours the reaction was complete. The mixture was washed with 50 mL of 0.4M Na2CO3 solution and then with 50 mL of saturated NH4Cl solution. The organic phase was dried over Na2SO4, filtered and the solvent removed under reduced pressure, affording 7.0 g of 4-isobutyryl-piperazine-1-carboxylic acid tert-butyl ester. The product was dissolved in 100 mL of DCM. H2SO4 (2.91 mL, 54.7 mmol) was added and the reaction left stirring for 16 hours. The precipitate formed was filtered affording 6.7 g of the titled compound (96%, yield)

Workup

  1. temperatureto warm up to room temperature and after 3 hours the reaction
  2. washThe mixture was washed with 50 mL of 0.4M Na2CO3 solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1a297ad6558f4d85ab9bf2cee9364f99
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

Loading…