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

HRID 2114331Notes

Reaction equation

HRID 2114331 reaction equation
CN.[C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1.[C:24]([BH3-])#[N:25].[Na+].C(O)(=O)C>C1COCC1>[C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:7][C:6]([CH:9]([NH:25][CH3:24])[CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 574186611-(4-Biphenylyl)-2-(4-morpholinyl)ethanone

Product 1

HCID 57425536[1-(4-Biphenylyl)-2-(4-morpholinyl)ethyl]methylamineYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.0 M methylamine solution in THF (18 mL, 36.0 mmol) was added to a solution of 1-(4-biphenylyl)-2-(4-morpholinyl)ethanone (2.52 g, 8.93 mmol ) in anhydrous THF (20 mL), The reaction mixture was stirred at room temperature for 1 h and then sodium cyanoborohydride (1.68 g, 26.79 mmol) and acetic acid (1 mL) were added. The resulting mixture was stirred at room temperature for 72 h until the starting material was consumed completely. At this point, saturated K2CO3 solution (40 mL) was added to and after stirring for 15 min, the solution was extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over Na2SO4 and concentrated. The resulting residue was isolated by column chromatography on silica gel (MeOH/EtOAc, 1:10) to yield [1-(4-biphenylyl)-2-(4-morpholinyl)ethyl]methylamine as an off-white solid(1.40 g, 53%), MS (ES) m/e 296[M+H]+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 72 h until the starting material
  2. customwas consumed completely
  3. additionAt this point, saturated K2CO3 solution (40 mL) was added to and
  4. stirringafter stirring for 15 min
  5. extractionthe solution was extracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting residue was isolated by column chromatography on silica gel (MeOH/EtOAc, 1:10)

Sources & evidence

ORD record
ord-17343c333cef4a60a2068314515f0eb4
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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