Pyrrolidine → 1-[4-(Chloromethyl)benzoyl]pyrrolidine

HRID 2266602Notes

Reaction equation

HRID 2266602 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(C(C)C)C(C)C)C>ClCCl.Cl>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 162268621-[4-(Chloromethyl)benzoyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloromethylbenzoyl chloride (5.0 g) and pyrrolidine (2.2 mL) in dichloromethane (30 mL) at 0° C. was treated with ethyldiisopropylamine (5.2 mL). The resulting mixture was warmed to room temperature over 1 hour and then stirred at this temperature for 2 hours. The mixture was diluted with 1.0 M aqueous hydrochloric acid, extracted with dichloromethane and the combined extracts washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound, 6.0 g.

Workup

  1. extractionextracted with dichloromethane
  2. washthe combined extracts washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-381ce6f390064a298ea592ff8ace8898
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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