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

HRID 279283Notes

Reaction equation

HRID 279283 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH:19]1[CH2:29][CH2:28][CH2:27][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]1>CC#N>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:19]2[CH2:29][CH2:28][CH2:27][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 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 iPr2NEt (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 NaHCO (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, C15H23ClNO2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionSaturated aqueous NaHCO (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-4c4c25d3feb94b35a25fec54be341d8a
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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