Betahistine → HCID 15287677, compound

HRID 275415Notes

Reaction equation

HRID 275415 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]([C:11]1[CH:12]=[C:13]([S:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]2[S:29][CH2:30][C:31](O)=[O:32])[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])[CH3:9].[CH3:34][NH:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1.C(N(CC)CC)C>C1C=CC=CC=1.O1CCCC1>[CH3:21][C:18]([C:15]1[CH:14]=[C:13]([S:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]2[S:29][CH2:30][C:31]([N:35]([CH3:34])[CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[O:32])[CH:12]=[C:11]([C:8]([CH3:7])([CH3:9])[CH3:10])[C:16]=1[OH:17])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 2366BetahistineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 9822857HCID 9822857, compound

Product 1

HCID 15287677HCID 15287677, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (0.13 g, 0.00105 moles) was added to a cold (10° C.) solution of trans-[[2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]cyclohexyl]thio]acetic acid (0.39 g, 0.00095 mole) in benzene (50 ml). The cold bath was removed and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated in vacuo to an oil. The oil was dissolved in toluene (50 ml) and then concentrated once again. The process was repeated using tetrahydrofuran (25 ml) in place of toluene. To a solution of the oil in tetrahydrofuran (50 ml) was added 2-(2-methylaminoethyl) pyridine (0.13 g, 0.00095 moles) and triethylamine (1 ml) and the reaction mixture was stirred at room temperature for 44 hours. After removal of the while solid precipitate by filtration, the filtrate was concentrated to give the crude product as an oil. The product was purified by silica gel chromatography.

Workup

  1. customThe cold bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo to an oil
  3. dissolutionThe oil was dissolved in toluene (50 ml)
  4. concentrationconcentrated once again
  5. stirringthe reaction mixture was stirred at room temperature for 44 hours
  6. customAfter removal of the while solid precipitate
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4e403e9a133249848eddc4d86dbbfdde
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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