Betahistine → HCID 13822937, compound

HRID 2082292Notes

Reaction equation

HRID 2082292 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:13][NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C(OCC)C>[CH3:13][N:14]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:1](=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 2366BetahistineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 13822937HCID 13822937, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acryloyl chloride (4.52 g, 0.05 mole) was added dropwise to a stirring solution of triethylamine (30 ml) and 2-(β-methylaminoethyl)pyridine (6.81 g, 0.05 mole) in ethyl ether (500 ml). After stirring overnight at room temperature, the white solid was removed by filtration and washed well with ethyl ether. The organic phases were combined, dried over sodium sulfate, filtered then concentrated to dryness to give an orange oil. The structure was confirmed by NMR.

Workup

  1. customthe white solid was removed by filtration
  2. washwashed well with ethyl ether
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthen concentrated to dryness
  6. customto give an orange oil

Sources & evidence

ORD record
ord-dfc60474c6fc4d5385697d931541882e
Source dataset
uspto-grants-1993_02
Patent number
US05189038

Reaction notes

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