Piperidine → HCID 21836525, compound

HRID 1739748Notes

Reaction equation

HRID 1739748 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>C(#N)C.[Cl-].[Na+].O>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 21836525HCID 21836525, compoundYield 0.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (see Preparation 54) (1.5 g, 1 mol. equiv.), piperidine (0.6 g, 1.5 mol. equiv.) and potassium carbonate (1.31 g, 2 mol. equiv.) in acetonitrile (20 ml) was heated under reflux under nitrogen for four hours. Saturated aqueous sodium bicarbonate solution and brine were added and the mixture extracted with ethyl acetate (2×40 ml). The organic extracts were combined and dried using magnesium sulphate. The organic solvent was removed under reduced pressure and the residue purified by flash column chromatography on silica gel eluting with methanol:dichloromethane (1:9, by volume) to give the title compound (0.65 g). TLC Rf=0.5 (silica, methanol:dichloromethane, 1:9, by volume). LRMS m/z=307(m+1)+. Found: C, 81.50; H, 8.51; N, 9,02. C21H26N2.0.06 CH2Cl2 requires C, 81.14; H, 8.45; N, 8.99%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for four hours
  3. extractionthe mixture extracted with ethyl acetate (2×40 ml)
  4. customdried
  5. customThe organic solvent was removed under reduced pressure
  6. customthe residue purified by flash column chromatography on silica gel eluting with methanol:dichloromethane (1:9, by volume)

Sources & evidence

ORD record
ord-eafdff4dbe754c088ad11e02f8cf6f22
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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