Morpholine → (5-Bromo-4-methylthiophen-2-yl)(morpholin-4-yl)methanone

HRID 606590

Reaktionsgleichung

Reaktionsgleichung von HRID 606590
CO[C:3]([C:5]1[S:6][C:7]([Br:11])=[C:8]([CH3:10])[CH:9]=1)=[O:4].[OH-].[Na+].BrC1SC(C(O)=O)=CC=1C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CCO.O.CN(C=O)C.CCOC(C)=O>[Br:11][C:7]1[S:6][C:5]([C:3]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:4])=[CH:9][C:8]=1[CH3:10]

Komponenten

11

Edukt 6

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2795489Methyl 5-bromo-4-methylthiophene-2-carboxylateHCID 218994595-Bromo-4-methylthiophene-2-carboxylic acid

Produkt 1

HCID 67047076(5-Bromo-4-methylthiophen-2-yl)(morpholin-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Bromo-4-methyl-thiophene-2-carboxylic acid methyl ester (8.51 mmol) was dissolved in EtOH (100 ml) and NaOH (42.5 mmol) added, as a 1M solution in water. Reaction was heated to 80° C. for 2 h, after which time all starting material had been consumed. Reaction was then concentrated in vacuo and the residue taken up in DCM and shaken with 1M HCl. The resulting biphasic mixture was then filtered and the filtrant washed with hexane and dried under vacuum. This gave 5-Bromo-4-methyl-thiophene-2-carboxylic acid as off white solid: m/z in MS AP−=219, 221 [M−H]−, 6.79 mmol, 80%. 5-Bromo-4-methyl-thiophene-2-carboxylic acid (6.79 mmol) was taken up in 30 ml DMF and morpholine (7.47 mmol), WSC.HCl (7.47 mmol) and HOBt (7.47 mmol) were added. Reaction was stirred at room temperature for 17 h and then diluted with EtOAc, washed with 1M HCl and brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography of the residue (silica, 33-50% EtOAc in hexane) gave (5-Bromo-4-methyl-thiophen-2-yl)-morpholin-4-yl-methanone as a pale golden oil: m/z in MS ES+=290, 292 [M+H]+, 4.67 mmol, 69%.

Aufarbeitung

  1. customReaction
  2. customafter which time all starting material had been consumed
  3. customReaction
  4. concentrationwas then concentrated in vacuo
  5. filtrationThe resulting biphasic mixture was then filtered
  6. washthe filtrant washed with hexane
  7. customdried under vacuum
  8. customReaction
  9. stirringwas stirred at room temperature for 17 h
  10. washwashed with 1M HCl and brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d96bba80fb7c4d03932edfc7208efdb1
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915300B2

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