Triethylamine → HCID 66855304, compound

HRID 1185459Notes

Reaction equation

HRID 1185459 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(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 66855304HCID 66855304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 15 g of Piperazine-1-carboxylic acid tert-butyl ester in 200 ml of DCM, 18 g of triethylamine was added and the mixture was cooled to 0° C. Then, 12.1 g of butyl chloroformate was slowly added. After the addition was completed the reaction mixture was allowed to warm to RT and to stir for 16 h. Then, 200 ml of DCM was added and the organic phase was washed two times with 0.1 M aqueous hydrochloric acid followed by saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was pure enough for the next reaction step. Yield: 21.9 g.

Workup

  1. additionAfter the addition
  2. temperatureto warm to RT
  3. washthe organic phase was washed two times with 0.1 M aqueous hydrochloric acid
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvents were removed under reduced pressure
  6. customThe crude product was pure enough for the next reaction step

Sources & evidence

ORD record
ord-03cb226ffdef4d0f880405dcb9751e47
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

Loading…