Benzyl Alcohol → HCID 68574100, compound

HRID 1296641Notes

Reaction equation

HRID 1296641 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[N:4][CH:3]=1.[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([O:22][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[N:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 86759066HCID 86759066, compound

Product 1

HCID 68574100HCID 68574100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (2S)-1-(6-chloro-2-pyrazinyl)-2-methylpiperazine (prepared in step 2 above; 0.16 g, 0.72 mmol) and benzyl alcohol (0.12 g, 1.1 mmol) in DMF (4 mL) was Na-t-BuO (0.14 g, 1.4 mmol) added and the mixture was stirred at 150° C. overnight. The solvent was evaporated off under reduced pressure and the residue taken up between CHCl3/H2O. The organic phase was concentrated and the crude product was purified by preparative C18-HPLC using acetonitrile/H2O/HOAc with UV detection at 254 nm. Yield: 1 mg (0.4%). MS m/z 284 (M)+. HRMS m/z calcd for C16H20N4O (M)+ 284.1637, found 284.1640.

Workup

  1. additionadded
  2. customThe solvent was evaporated off under reduced pressure
  3. concentrationThe organic phase was concentrated
  4. customthe crude product was purified by preparative

Sources & evidence

ORD record
ord-3fad84b7126d4234b7b96a283ddbe675
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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