N,N-Dimethylethylenediamine → HCID 86595872, compound

HRID 857900Notes

Reaction equation

HRID 857900 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[NH:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].[CH:19](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:20].CN(C)CCN>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[N:11]([CH:19]=[O:20])[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylateHCID 12169650HCID 12169650, compound

Product 1

HCID 86595872HCID 86595872, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (38.22 g, prepared according to the procedure described in WO 96/31478 Step B page 94) in dry dichloromethane (400 mL) was treated with pentafluorophenyl formate (43.32 g, prepared according to the procedure of Kisfaludy and Otvos, Synthesis, 1987, 510). After stirring at room temperature overnight the reaction mixture was treated with N,N-dimethylethylenediamine (32.5 mL) and stirring continued for a further 1.5 hours. The reaction mixture was then washed with 1 M hydrochloric acid (400 mL), then a saturated solution of sodium hydrogen carbonate (400 mL), then water (400 mL), dried over sodium sulfate and then evaporated. The residue was triturated with a mixture of diethyl ether and pentane to give the title compound (27.21 g) as an off white solid, MS: 309 [MNa]+.

Workup

  1. customprepared
  2. customaccording to the procedure of Kisfaludy and Otvos, Synthesis, 1987, 510)
  3. stirringstirring
  4. waitcontinued for a further 1.5 hours
  5. washThe reaction mixture was then washed with 1 M hydrochloric acid (400 mL)
  6. dry with materiala saturated solution of sodium hydrogen carbonate (400 mL), then water (400 mL), dried over sodium sulfate
  7. customevaporated
  8. customThe residue was triturated with a mixture of diethyl ether and pentane

Sources & evidence

ORD record
ord-4a1cf459e84b4e9fb4aa6937d3c3fcfb
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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