Cesium carbonate → HCID 18727005, compound

HRID 1418376Notes

Reaction equation

HRID 1418376 reaction equation
[CH2:1]1[O:10][C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[O:3][CH2:2]1.Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]1[O:10][C:4]2([CH2:9][CH2:8][N:7]([C:12]3[S:13][CH:14]=[CH:15][N:16]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 764302-Bromothiazole

Product 1

HCID 18727005HCID 18727005, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Piperidone ethylene ketal (2.0 ml, 16 mmol), 2-bromothiazole (2.68 g) and caesium carbonate (8.9 g) in DMF (20 ml) were heated at 90°-100° C. for 16 h . The cooled mixture was diluted with water, extracted twice with ether, the ether layers washed with water six times, dried over sodium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting with 50% ether/hexane to afford the title compound as a pale yellow oil (2.2 g), MS (+EI) 226 (M+), 1H NMR (CDCl3) 7.17 (1H, d, 3.6 Hz), 6.55 (1H, d, 3.6 Hz), 4.00 (4H, s), 3.65-3.61 (4H, m), 1.83-1.80 (4H, m).

Workup

  1. extractionextracted twice with ether
  2. washthe ether layers washed with water six times
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica eluting with 50% ether/hexane

Sources & evidence

ORD record
ord-00be7d23f7d24caa9fb8f8b5fe79d856
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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