1-Chloro-4-(chloromethyl)benzene → HCID 2838484, compound

HRID 2187798Notes

Reaction equation

HRID 2187798 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[NH:10]1[CH2:20][CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11]1>CC#N>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:20][CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 98969Ethyl nipecotate

Product 1

HCID 2838484HCID 2838484, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-chlorobenzyl chloride (6.42 g, 39.9 mmol) and 1Pr2NEt (7.74 g, 40.0 mmol) were added to a solution of ethyl nipecotate (6.29 g, 40.0 mmol) in CH3CN (15 mL). The reaction mixture was stirred at 70° C. for 1.5 h. The solvent was removed under reduced pressure. Saturated aqueous NaHCO3 (50 mL) was added to the residue and the mixture was extracted with EtOAc (100 mL). The organic phase was washed with saturated aqueous NaHCO3 and brine, and dried over Na2SO4. The solvent was removed under reduced pressure to afford ethyl 1-(4-chlorobenzyl)nipecotate as a red yellow oil (11.025 g, 97.8%) used without further purification. The purity was determined by RPLC/MS (97%); ESI/MS m/e 382.2 (M++H, C15H21ClNO2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionSaturated aqueous NaHCO3 (50 mL) was added to the residue
  3. extractionthe mixture was extracted with EtOAc (100 mL)
  4. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5f58d7ce419f462aa64f89e3b1b419fa
Source dataset
uspto-grants-2002_06
Patent number
US06410566B1

Reaction notes

Loading…