Methylamine → (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine

HRID 68615

Reaktionsgleichung

Reaktionsgleichung von HRID 68615
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH:2][CH3:1])=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 230102233-Bromo-4-((4-methoxybenzyl)oxy)benzaldehyde

Produkt 1

HCID 63045147(4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2M methylamine in MeOH (30 mL) was added intermediate 32 (2.91 g, 9.1 mmol, 1 eq). After stirring this mixture at room temperature for 30 min, the solvent was removed and the residue was partitioned between saturated NaHCO3 and DCM (2×100 mL). The organic layer was dried (Na2SO4) and concentrated. The resultant residue was dissolved in MeOH (25 mL) and, after addition of sodium borohydride (1.0 g, 27.6 mmol, 3 eq), the mixture was stirred at room temperature for 1 h. Solvent was removed and the residue was partitioned between a Na2CO3 solution and CHCl3. The resultant organic layer was dried (Na2SO4) and concentrated in vacuo to give 2.7 g, (88%) of (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine (33).

Aufarbeitung

  1. customthe solvent was removed
  2. customthe residue was partitioned between saturated NaHCO3 and DCM (2×100 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe resultant residue was dissolved in MeOH (25 mL)
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customSolvent was removed
  8. customthe residue was partitioned between a Na2CO3 solution and CHCl3
  9. dry with materialThe resultant organic layer was dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2e2bdbd81f0c4e6ea906aa73e3b13f53
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822467B2

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