Hydrochloric Acid → HCID 68310211, compound

HRID 1021256Notes

Reaction equation

HRID 1021256 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C1COCC1.Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:19]1[CH2:20][CH2:21][N:16]([C:12]2[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 86686223HCID 86686223, compound

Product 1

HCID 68310211HCID 68310211, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl]-4-(pyridin-2-yl)piperazine (240 mg) was mixed with THF (2 ml), and a 1 M hydrochloric acid (2 ml) was added thereto, followed by stirring at room temperature for 5 hours. A saturated aqueous sodium hydrogen carbonate solution and CHCl3 were added to the reaction mixture, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain {3-[4-(pyridin-2-yl)piperazin-1-yl]phenyl}methanol (166 mg).

Workup

  1. dry with materialthe organic layer was dried over MgSO4
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d04ca9cd2f564d50bc1f361b81982bcf
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

Loading…