Iodine → HCID 68408396, compound

HRID 2387946Notes

Reaction equation

HRID 2387946 reaction equation
[Mg].II.Br[CH2:5][CH2:6][CH2:7]C.[CH2:9]([N:16]1[CH2:21][CH2:20][C:19]([N:24]([CH3:26])[CH3:25])([C:22]#N)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH4+].[Cl-]>CCOCC.C1COCC1.CO.C(Cl)(Cl)Cl>[CH2:9]([N:16]1[CH2:17][CH2:18][C:19]([CH2:22][CH2:5][CH2:6][CH3:7])([N:24]([CH3:25])[CH3:26])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 807IodineHCID 8002Butyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 164539151-Benzyl-4-(dimethylamino)piperidine-4-carbonitrile

Product 1

HCID 68408396HCID 68408396, compoundYield 53.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a mixture of 17.7 g (6 equiv.) of magnesium and 50 ml of dry ether there were added first a small amount of iodine and then, over a period of 1 hour, 100 g (6 equiv.) of bromobutane dissolved in 100 ml of dry ether. This reaction mixture was stirred for 1 hour at room temperature. The Grignard reagent prepared above was added over a period of 20 minutes to a solution of 30 g (1 equiv.) of 1-benzyl-4-(dimethylamino)piperidine-4-carbonitrile dissolved in 210 ml of dry THF, and the resulting reaction mixture was then stirred for 12 hours at room temperature. The progress of the reaction was monitored by thin-layer chromatography (10% MeOH/CHCl3). When the reaction was complete, the reaction solution was cooled to 0° C.; saturated NH4Cl solution was added, the mixture was filtered over Celite and extracted with ethyl acetate (3×200 ml), and the combined organic phases were dried over Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (aluminium oxide neutral; hexane). 18.2 g (53%) of product were obtained in the form of an oil.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas then stirred for 12 hours at room temperature
  3. temperaturethe reaction solution was cooled to 0° C.
  4. filtrationthe mixture was filtered over Celite
  5. extractionextracted with ethyl acetate (3×200 ml)
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customAfter removal of the solvent
  8. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-074fc0482100479382204fb4c16d4a0c
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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