Methylamine → tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

HRID 23713

Reaction equation

HRID 23713 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[CH3:17][NH2:18].[C:19](=[O:30])(OC(C)(C)C)[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][N:18]([CH3:17])[C:19](=[O:30])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 27953572-Bromo-1-(4-morpholinophenyl)ethanoneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 22574343tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamateYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo-1-(4-morpholin-4-ylphenyl)ethanone (Tetrahedron Letters; 39, (1998), 4987-4990)(3.40 g, 11.97 mmol) was dissolved in dry THF (30 ml) under N2 and cooled in ice. A 2M solution of methylamine in THF (12 ml, 24 mmol) was added and the reaction stirred for 1 hr. The mixture was filtered and the filtrate treated with di-t-butyl carbonate (2.61 g, 12 mmol) at ice temperature. Stirring was continued for 24 hr then the solvent evaporated. Chromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc gave the product as a pale yellow solid (1.53 g, 38%): mp87-89°.

Workup

  1. temperaturecooled in ice
  2. filtrationThe mixture was filtered
  3. stirringStirring
  4. waitwas continued for 24 hr
  5. customthe solvent evaporated
  6. washChromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc

Sources & evidence

ORD record
ord-14a1a40fce874bbd8bc183963b270f71
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

Loading…