Triethylamine → HCID 89938204, compound

HRID 2200370Notes

Reaction equation

HRID 2200370 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH:22]1[CH2:26][CH2:25][C:24]([C:27]#[N:28])=[CH:23]1>CN(C)C=O.O>[C:27]([C:24]1[CH2:25][CH2:26][C@@H:22]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:23]=1)#[N:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 1264506674201-92-6

Product 1

HCID 89938204HCID 89938204, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl piperazine-1-carboxylate (59.5 g, 320 mmol) in dimethyl formamide (400 ml) was added triethylamine (134 ml, 959 mmol) at 25° C. and stirred the reaction mixture for 10 minutes. To this was added 3-bromocyclopent-1-enecarbonitrile (55 g, 320 mmol) and the reaction mixture was stirred for 3 h. The progress of reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue obtained was diluted with water (250 ml) and extracted with ethyl acetate (3×250 ml). The combined organic layer was dried over anhydrous sodium sulphate. The solvent in the organic layer was evaporated under reduced pressure to obtain crude product. The crude product purified by flash column chromatography over silica gel (100-200 mesh) using 40% ethyl acetated in hexane as an eluent to obtain the title compound (35 g, 126 mmol, 39.5% yield).

Workup

  1. stirringthe reaction mixture was stirred for 3 h
  2. customThe progress of reaction
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customThe residue obtained
  5. extractionextracted with ethyl acetate (3×250 ml)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  7. customThe solvent in the organic layer was evaporated under reduced pressure
  8. customto obtain crude product
  9. customThe crude product purified by flash column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-9b83cbd569f74a49a87184d9663fb53a
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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