Triethylamine → HCID 53831000, compound

HRID 2380575Notes

Reaction equation

HRID 2380575 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.Cl.Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][C:26]([OH:28])=O)[CH2:19][CH2:18]1.C([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])C>ClCCl.CN(C)C=O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:24]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][C:26]([N:37]2[CH2:38][CH2:39][CH2:2][CH2:1][CH2:41][CH2:40]2)=[O:28])[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70187119HCID 70187119, compound

Product 1

HCID 53831000HCID 53831000, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (3.50 ml) was added to a suspension of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-3-phenylbut-2-enoic acid dihydrochloride (4.17 g, 9.81 mmol) in dichloromethane (50 ml) and a few drops of dry N,N-dimethyl formamide added. After stirring at room temperature for 3 h, the solid formed was filtered off and a solution of triethylamine (3.07 g, 30.4 mmol) and hexamethyleneimine (1.07 g, 10.8 mmol) in dichloromethane (25 ml) was added dropwise to an ice-cooled suspension of the filtered solid in dichloromethane (50 ml). The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The crude product was chromatographed on silica gel, eluting with ethyl acetate: pentane (1:1 to 2:1) to afford the title compound as two isomers. The Z-isomer was obtained as an oil and this was dissolved in diethyl ether and acidified with ethereal hydrogen chloride to afford a colourless hygroscopic powder which was recrystallised from dichloromethane-diisopropylether to give the dihydrochloride as a colourless powder (0.36 g), m.p. 149.4° to 152.9° C.

Workup

  1. additionadded
  2. customthe solid formed
  3. filtrationwas filtered off
  4. temperaturecooled
  5. stirringThe reaction mixture was stirred at room temperature for 2 h
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was chromatographed on silica gel
  8. washeluting with ethyl acetate: pentane (1:1 to 2:1)

Sources & evidence

ORD record
ord-6cc5c5fdd31f42cf81f4a203bb33bbb7
Source dataset
uspto-grants-1994_11
Patent number
US05369103

Reaction notes

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