Triethylamine → HCID 66855424, compound

HRID 1970557Notes

Reaction equation

HRID 1970557 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH:13]1([OH:17])[CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.[N:25]1([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>ClCCl>[CH:13]1([O:17][C:2]([N:28]2[CH2:29][CH2:30][N:25]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])[CH2:26][CH2:27]2)=[O:4])[CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 76218CyclobutanolHCID 94429TriphosgeneHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 66855424HCID 66855424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.6 g triphosgene and 1.7 ml cyclobutanol in 40 ml dichloromethane were added 6.2 ml triethylamine dropwise at 0° C. After 30 minutes 4.4 ml benzyl 1-piperazinecarboxylate and 3.2 ml triethylamine were added at 0° C. The reaction mixture was allowed to warm to RT for 16 h. Excess triphosgene was destroyed by adding a solution of 2 g NaOH in 200 ml water and stirring for 2 h. The layers were separated, the organic layer dried over MgSO4 and concentrated. The crude product thus obtained was purified by chromatography on silica using heptane/ethyl acetate 4/1 to 2/1 as eluent.

Workup

  1. customExcess triphosgene was destroyed
  2. additionby adding a solution of 2 g NaOH in 200 ml water
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c13e10a1a5024dd9a9ac90f88419b5db
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…