Triethylamine → HCID 53263189, compound

HRID 1290878Notes

Reaction equation

HRID 1290878 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Br.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:21](=[C:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]=2[CH:28]=1.C(N(CC)CC)C>C1COCC1>[CH3:1][O:2][C:3](=[O:6])[CH2:4][N:25]1[CH2:24][CH2:23][C:22](=[C:21]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH2:14][CH2:13][C:12]3[CH:28]=[C:8]([Cl:7])[CH:9]=[CH:10][C:11]2=3)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 124087Desloratadine

Product 1

HCID 53263189HCID 53263189, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylbromoacetate (0.17 ml, 1.77 mmol) was added dropwise to a solution of 4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}-piperidine (0.50 g, 1.61 mmol) and triethylamine (0.45 ml, 3.22 mmol) in THF (15 ml) under an inert atmosphere. The reaction was left to stir for 18 hours. THF was removed under reduced pressure and the product purified by column chromatography on silica gel, eluting with 5% methanol/DCM. Product containing fractions were combined and solvent removed under reduced pressure to yield methyl-[4-{8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene}-piperidin-1-yl]acetate as an orange solid (550 mg, 90%).

Workup

  1. waitThe reaction was left
  2. customTHF was removed under reduced pressure
  3. customthe product purified by column chromatography on silica gel
  4. washeluting with 5% methanol/DCM
  5. additionProduct containing fractions
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-7d2138ee6cd64ba085786d88e443580c
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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