Acetonitrile → 2-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine

HRID 133570Notes

Reaction equation

HRID 133570 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1.C(#N)C.Cl.[NH:21]1[CH2:28][CH2:27][CH2:26][CH:22]1[C:23]([NH2:25])=[O:24]>ClCCl>[C:23]([CH:22]1[CH2:26][CH2:27][CH2:28][N:21]1[CH2:13][C:12]1[CH:15]=[CH:16][C:9]([Cl:8])=[CH:10][CH:11]=1)(=[O:24])[NH2:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 3016353Pyrrolidine-2-carboxamide hydrochloride

Product 1

HCID 184262722-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Triethylamine (7.45 mL) and 4-chlorobenzyl chloride (3.88 g, 24.1 mmol) were added to an acetonitrile (35 mL) solution of dl-prolinamide hydrochloride (2.5 g, 21.8 mmol). The resulting reaction mixture was stirred at 70° C. for 4 hours and subsequently stirred at 25° C. for 16 hours. The resulting mixture was diluted with dichloromethane (20 mL) and washed with water (30 mL×3). The organic layer was dried (over MgSO4) and concentrated. The obtained crude product was purified by chromatography (SiO2, methanol-dichloromethane) to thereby provide 2-carbamoyl-1-(4-chlorobenzyl)pyrrolidine (5.21 g, 81%).

Workup

  1. customThe resulting reaction mixture
  2. stirringsubsequently stirred at 25° C. for 16 hours
  3. washwashed with water (30 mL×3)
  4. dry with materialThe organic layer was dried (over MgSO4)
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by chromatography (SiO2, methanol-dichloromethane) to thereby provide 2-carbamoyl-1-(4-chlorobenzyl)pyrrolidine (5.21 g, 81%)

Sources & evidence

ORD record
ord-27212f5383af45468743ef003e9abb01
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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