Water → HCID 10402058, compound

HRID 1667319Notes

Reaction equation

HRID 1667319 reaction equation
C(N(CC)CC)C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1/[CH:21]=[CH:22]/[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.O>O1CCCC1>[Cl:8][CH2:9][C:10]([N:26]1[CH2:27][CH2:28][CH:23](/[CH:22]=[CH:21]/[C:15]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:14]=2[CH3:13])[CH2:24][CH2:25]1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 10082008HCID 10082008, compound

Product 1

HCID 10402058HCID 10402058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, 6.77 ml of triethylamine and 3.87 ml of chloroacetyl chloride were added to a solution of 9.96 g of 4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine in 150 ml of tetrahydrofuran. After stirring at ambient temperature for 20 minutes, 200 ml of water was added to the mixture. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether. The combined organic layer was and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate). The collected crystals were washed with diisopropyl ether-hexane and dried under reduced pressure to give 10.69 g of 1-(chloroacetyl)-4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine.

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  6. washThe collected crystals were washed with diisopropyl ether-hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-05e0356ef447498987c63e9fb63a8663
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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