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

HRID 2114379Notes

Reaction equation

HRID 2114379 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.CN.[C:24]([BH3-])#[N:25].[Na+].C(O)(=O)C>C1COCC1.C(OCC)(=O)C>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:25][CH3:24])[CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1

Participants

7

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 103.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-biphenylyl)-2-(4-morpholinyl)ethanone (9.70 g, 34.4 mmol) in THF (100 ML) was added methylamine (2M solution in THF, 100 mL, 200 mmol). The mixture was stirred at room temperature for 15 min and then sodium cyanoborohydride (8.34 g, 133 mmol) and acetic acid (2.0 mL) were added. The resultant mixture was stirred at room temperature for 48 h. The mixture was diluted with ethyl acetate (200 mL) and washed with 5% NaHCO3 (200 mL) and water (200 mL). The organic layer was dried (MgSO4) and concentrated to give 10.59 g (100%) of the title compound as a yellow oil which solidified upon standing at room temperature. MS (ES) m/e 297.6 [M+H]+.

Workup

  1. washwashed with 5% NaHCO3 (200 mL) and water (200 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c88804447b2d461788864720dfc6aac2
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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