Triethylamine → 4-[4-(4-Bromophenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acid

HRID 1005843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005843
C[O:2][C:3]([C:5]1([CH2:11][S:12](Cl)(=[O:14])=[O:13])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].Cl.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([S:12]([CH2:11][C:5]3([C:3]([OH:2])=[O:4])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)(=[O:14])=[O:13])[CH2:26][CH2:25]2)=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 144228381-(4-Bromophenyl)piperazine hydrochlorideHCID 22228396Methyl 4-[(chlorosulfonyl)methyl]oxane-4-carboxylate

Produkt 1

HCID 226466794-[4-(4-Bromophenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acidAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Chlorosulfonylmethyltetrahydropyran-4-carboxylic acid methyl ester (5.10 g) was added to a stirred suspension of 4-bromophenylpiperazine hydrochloride (5.51 g) and triethylamine (6.09 ml) in dichloromethane (120 ml), and the mixture was stirred at room temperature for 18 h. The dichloromethane was then removed under reduced pressure, and the residue redissolved in tetrahydrofuran (60 ml), methanol (30 ml) and water (15 ml), treated with lithium hydroxide monohydrate (4.15 g) and heated to reflux for 2 h. The organic solvents were removed in vacuo and the residue was diluted with 1 M sodium hydroxide (30 ml) and washed with diethyl ether (3×40 ml). The aqueous phase was then acidified to pH 4-5 with citric acid, forming a white precipitate, which was filtered, washed with water and dried to constant weight under vacuum at 40° C. to provide the title compound as a white solid (4.55 g, 51%).

Aufarbeitung

  1. customThe dichloromethane was then removed under reduced pressure
  2. dissolutionthe residue redissolved in tetrahydrofuran (60 ml)
  3. additionmethanol (30 ml) and water (15 ml), treated with lithium hydroxide monohydrate (4.15 g)
  4. temperatureheated
  5. temperatureto reflux for 2 h
  6. customThe organic solvents were removed in vacuo
  7. additionthe residue was diluted with 1 M sodium hydroxide (30 ml)
  8. washwashed with diethyl ether (3×40 ml)
  9. customforming a white precipitate, which
  10. filtrationwas filtered
  11. washwashed with water
  12. customdried to constant weight under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-615eccb81bc14b2bb31dc91b12d69583
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787536B2

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