Sodium Bicarbonate → HCID 68310238, compound

HRID 2171634Notes

Reaction equation

HRID 2171634 reaction equation
[C:1](=[O:4])([O-])O.[Na+].Cl.Cl.[N:8]1([C:14]2[CH:15]=[C:16]([CH2:20][OH:21])[CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>C(Cl)(Cl)Cl>[O:4]1[CH2:1][CH2:18][CH:19]([N:11]2[CH2:12][CH2:13][N:8]([C:14]3[CH:15]=[C:16]([CH2:20][OH:21])[CH:17]=[CH:18][CH:19]=3)[CH2:9][CH2:10]2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69804337HCID 69804337, compound

Product 1

HCID 68310238HCID 68310238, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were added to [3-(piperazin-1-yl)phenyl]methanol dihydrochloride (240 mg) to carry out liquid separation. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was mixed with dichloromethane (5 ml), and tetrahydro-4H-pyran-4-one (100 mg) and acetic acid (168 mg) were added thereto, followed by stirring at room temperature for 15 minutes. Sodium triacetoxyborohydride (576 mg) was added to the reaction mixture at 0° C., followed by stirring at room temperature for 5 hours. Water and CHCl3 were added to the reaction mixture, and the aqueous layer was adjusted to a pH of 8 to 9 by the addition of a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with water, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain {3-[4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl]phenyl}methanol (45 mg).

Workup

  1. customliquid separation
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained residue was mixed with dichloromethane (5 ml), and tetrahydro-4H-pyran-4-one (100 mg) and acetic acid (168 mg)
  5. additionwere added
  6. additionSodium triacetoxyborohydride (576 mg) was added to the reaction mixture at 0° C.
  7. stirringby stirring at room temperature for 5 hours
  8. additionWater and CHCl3 were added to the reaction mixture
  9. additionthe aqueous layer was adjusted to a pH of 8 to 9 by the addition of a saturated aqueous sodium hydrogen carbonate solution
  10. washThe organic layer was washed with water
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-33662dbc0d2145eea6774b061c3996f6
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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