Sodium Chloride → N-(2-Propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

HRID 371159Notes

Reaction equation

HRID 371159 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:29][C@@H:28]([OH:30])[CH2:27][CH2:26][NH:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:32][CH:33]=[CH2:34].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>C(O)C>[CH2:34]([N:25]1[CH2:26][CH2:27][C@H:28]([OH:30])[CH2:29][C@@H:24]1[C:10]1[CH:11]=[CH:12][C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:33]=[CH2:32]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 70413103Cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

Product 1

HCID 70490735N-(2-Propenyl)-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinolYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 778 mg (1.90 mmole) of cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol, 160 microliters (1.84 mmole) of 1-bromo-2-propene and 300 mg (2.17 mmole) of potassium carbonate in 10 ml ethanol is stirred at 25° C. for 20.5 hours. An additional 4 microliters of 1-bromo-2-propene is added to the reaction and stirring continued for 7 hours. The reaction mixture is then added to 50 ml saturated sodium chloride and extracted with 250 ml ethyl ether. The ether extract is dried over magnesium sulfate and the solvent is evaporated. The resulting oil is purified via column chromatography on 28 g of silica gel eluted in 7 ml fractions with 1:3 methanol/ethyl ether to yield (fractions 10-35) 518 mg (61%) of the title compound as an oil.

Workup

  1. stirringstirring
  2. waitcontinued for 7 hours
  3. extractionextracted with 250 ml ethyl ether
  4. extractionThe ether extract
  5. dry with materialis dried over magnesium sulfate
  6. customthe solvent is evaporated
  7. customThe resulting oil is purified via column chromatography on 28 g of silica gel
  8. washeluted in 7 ml fractions with 1:3 methanol/ethyl ether

Sources & evidence

ORD record
ord-2ed4053db0bb40a18647370a4467efbd
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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