Diisopropylethylamine → HCID 68600587, compound

HRID 1185551Notes

Reaction equation

HRID 1185551 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[F:13][C:14]([F:19])([F:18])[CH2:15][CH2:16][OH:17].CCN(C(C)C)C(C)C.[N:29]1([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>ClCCl>[F:13][C:14]([F:19])([F:18])[CH2:15][CH2:16][O:17][C:2]([N:32]1[CH2:33][CH2:34][N:29]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[CH2:30][CH2:31]1)=[O:4]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 1375123,3,3-Trifluoro-1-propanolHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 68600587HCID 68600587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.1 g triphosgene and 2.3 ml 3,3,3-trifluoropropan-1-ol in 70 ml dichloromethane were added 9.0 ml DIPEA dropwise at 0° C. After 30 minutes 5.1 ml benzyl 1-piperazinecarboxylate and 34.5 ml DIPEA were added at 0° C. The reaction mixture was allowed to warm to RT overnight. Excess triphosgene was destroyed by adding a solution of 2.5 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. Yield: 3.2 g.

Workup

  1. customExcess triphosgene was destroyed
  2. additionby adding a solution of 2.5 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-cd03afd3438a4c6084d9770fcfbaf9df
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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