Ethyl bromoacetate → HCID 54519729, compound

HRID 484317Notes

Reaction equation

HRID 484317 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:16](=[C:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8][C:7]=2[CH:23]=1)#[N:2].C(N(CC)CC)C.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:16](=[C:17]3[CH2:22][CH2:21][N:20]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:19][CH2:18]3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH2:9][CH2:8][C:7]=2[CH:23]=1)#[N:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 19747228HCID 19747228, compound

Product 1

HCID 54519729HCID 54519729, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dry THF (20 ml) was added to 0.4 g of 8-cyano-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine to dissolve the latter, followed by the addition of 0.2 g of triethylamine and 0.27 g of ethyl bromoacetate. The resultant mixture was stirred at room temperature for 24 hours. After the completion of the reaction, THF was distilled off under reduced pressure, the residue was dissolved in chloroform, and the resultant solution was washed with water. The chloroform layer was dried over anhydrous Na2SO4 and then filtered. The chloroform was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol (20:1), 0.5 g of 8-cyano-11-(1-ethoxycarbonylmethyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 97%).

Workup

  1. dissolutionto dissolve the latter
  2. distillationwas distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washthe resultant solution was washed with water
  5. dry with materialThe chloroform layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. distillationThe chloroform was distilled off under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
  9. washeluted with chloroform:methanol (20:1)

Sources & evidence

ORD record
ord-5459fe61ea8540e8b176ecb30a487379
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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