Acetic Acid → [1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

HRID 2114347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114347
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.CN.[C:19]([BH3-])#[N:20].[Na+].C(O)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:20][CH3:19])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 208237461-(3-Bromophenyl)-2-(4-morpholinyl)ethanone

Produkt 1

HCID 57501274[1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-bromophenyl)-2-(4-morpholinyl)ethanone (7.8 g, 27.0 mmol) in THF (50 mL) was added methylamine (100 mL, 200 mmol, 2M solution in THF). After stirring for 15 min at room temperature, sodium cyanoborohydride (3.40 g, 54 mmol) was added followed by acetic acid (2 mL). The resultant mixture was stirred at RT for 5 days. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with 5% NaHCO3 (200 mL) and brine (200 mL). The organic layer was dried (MgSO4) and concentrated to give [1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine as yellow oil (8.10 g, 100%) which solidified after standing at room temperature. MS (ESI): 299.6 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with 5% NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af173e9b66af485e88b2a2aae1d99e84
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432258B2

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