1-Phenethylamine, (+)- → HCID 178424226, compound

HRID 1294707Notes

Reaction equation

HRID 1294707 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])#[N:2].[C:16]1([C@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:1]([N:3]=[C:4]([NH:24][C@@H:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])#[N:2]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 86093122Ethyl n-cyano-2-(2-methylphenyl)ethanimidoate

Product 1

HCID 178424226HCID 178424226, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 26B (142 mg, 0.7 mmol) and (R)-1-phenylethylamine (85 mg, 0.7 mmol) in absolute ethanol (1 mL) was stirred at 60° C. for 6 h. The mixture was concentrated under reduced pressure and purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile in 10 mM of ammonium acetate over 15 min at a flow rate of 70 mL/min to provide the title compound. MS (ESI+) m/z 277 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.46 (d, J=6.78 Hz, 3H) 2.28 (s, 3H) 3.83 (s, 2H) 5.10 (m, 1H) 6.95 (d, J=8.48 Hz, 1H) 7.16 (m, 3H) 7.29 (m, 1H) 7.35 (m, 5H) 9.37 (d, J=7.46 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)
  3. customover 15 min

Sources & evidence

ORD record
ord-837a6d2f91e64dde89291e375dc0377e
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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