1-Acetoxy-2-bromoethane → HCID 14554136, compound

HRID 1290879Notes

Reaction equation

HRID 1290879 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[C:22](=[C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH2:15][CH2:14][C:13]=2[CH:29]=1>C1COCC1>[CH2:5]([O:4][C:1](=[O:3])[CH2:2][N:26]1[CH2:25][CH2:24][C:23](=[C:22]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH2:15][CH2:14][C:13]3[CH:29]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]2=3)[CH2:28][CH2:27]1)[CH3:6]

Participants

4

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 124087Desloratadine

Product 1

HCID 14554136HCID 14554136, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromoethyl acetate (267 mg, 1.6 mmol) was added dropwise to a stirred solution of 4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}piperidine (500 mg, 1.6 mmol) in THF (12 ml) and the reaction stirred at room temperature overnight. THF was removed under reduced pressure and the residue partitioned between ethylacetate and saturated sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulphate, filtered and solvent removed to leave a white solid. The product was purified by column chromatography on silica gel eluting with 5% methanol/DCM. Product containing fractions were combined and solvent removed to yield ethyl-(4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidin-1-yl)acetate as a white solid (214 mg, 34%)

Workup

  1. customTHF was removed under reduced pressure
  2. customthe residue partitioned between ethylacetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customsolvent removed
  7. customto leave a white solid
  8. customThe product was purified by column chromatography on silica gel eluting with 5% methanol/DCM
  9. additionProduct containing fractions
  10. customsolvent removed

Sources & evidence

ORD record
ord-b5a776ff601f4440991c68a791af2380
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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