1-Hydroxybenzotriazole → HCID 86686216, compound

HRID 2171649Notes

Reaction equation

HRID 2171649 reaction equation
[F:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:22][OH:23].CCN=C=NC[CH2:30][CH2:31]N(C)C.Cl.C1C=CC2N([OH:45])N=NC=2C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.ClCCCl.C(O)(=O)C>[F:1][C:2]1[C:3]([CH2:22][OH:23])=[CH:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:30](=[O:45])[CH3:31])[CH2:18][CH2:17]2)[CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86686217HCID 86686217, compound

Product 1

HCID 86686216HCID 86686216, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

(2-Fluoro-3-{4-[2-(piperidin-4-yl)ethyl]piperidin-1-yl}phenyl)methanol (200 mg) and acetic acid (63 mg) were mixed with DCE (3 ml), and WSC hydrochloride (220 mg) and HOBt (155 mg) were added thereto, followed by stirring at room temperature for 3 hours. A saturated aqueous sodium hydrogen carbonate solution and CHCl3 were added to the reaction mixture, and the organic layer was liquid separation and concentrated under reduced pressure. The obtained residue was mixed with MeOH (3 ml), and a 1M aqueous NaOH solution (1 ml) was added thereto, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain 1-[4-(2-{1-[2-fluoro-3-(hydroxymethyl)phenyl]piperidin-4-yl}ethyl)piperidin-1-yl]ethanon e (211 mg).

Workup

  1. additionwere added
  2. customliquid separation
  3. concentrationconcentrated under reduced pressure
  4. additionThe obtained residue was mixed with MeOH (3 ml)
  5. additiona 1M aqueous NaOH solution (1 ml) was added
  6. stirringby stirring at room temperature for 30 minutes
  7. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3
  8. additiona saturated aqueous sodium hydrogen carbonate solution were then added
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-2b33923ac9134e55b90c7ae31311aa6b
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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