Benzyl Chloride → HCID 18338481, compound

HRID 2298439Notes

Reaction equation

HRID 2298439 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]1>C(O)(=O)C>[CH2:1]([N:15]1[CH2:16][CH2:17][CH:18]([CH2:21][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 124623861,3-Diethyl 2-(4-piperidinylmethyl)propanedioate

Product 1

HCID 18338481HCID 18338481, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
62.5 °C

Procedure

Benzyl chloride (54.4 g) and sodium carbonate (149.4 g) were added to the solution of the acetic acid salt of diethyl (4-piperidylmethyl)malonate [XXIXb] from the previous step. The obtained slurry was stirred for 12 hours at 60-65° C. and evaporated under reduced pressure. Water was added to the residue and the obtained mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, passed through short silica gel column and evaporated under reduced pressure. The obtained residue was washed with hexanes and dried under reduced pressure to give diethyl (N-benzyl-4-piperidylmethyl)malonate [XXIIb].

Workup

  1. customevaporated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe obtained mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. washThe obtained residue was washed with hexanes
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-17333962149b4873b781260e413c8c90
Source dataset
uspto-grants-2002_12
Patent number
US06492522B1

Reaction notes

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