1,1'-Carbonyldiimidazole → 3,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-(phenylmethyl)benzenepropanamide

HRID 2256315Notes

Reaction equation

HRID 2256315 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:18])=[O:16])[CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:14][C:15]([N:17]([CH3:18])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 190293143,4-Dichloro-beta-[2-[(phenylmethyl)methylamino]-2-oxoethyl]benzenepropanoic acid

Product 1

HCID 190293813,4-Dichloro-beta-(2-hydroxyethyl)-N-methyl-N-(phenylmethyl)benzenepropanamideYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3,4-Dichloro-beta-[2-[(phenylmethyl)methylamino]-2-oxoethyl]benzenepropanoic acid (6.9 g) in EtOAc (150 mL) was treated with carbonyldiimidazole (4.4 g) and N,N-dimethylaminopyridine (0.22 g). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for 1 hour. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (4.46 g) in H2O (75 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was then diluted with EtOAc (250 mL) and washed with 1N HCl (250 mL), H2O (250 mL) and dried over MgSO4, filtered and concentrated under reduced pressure to yield the title compound (6.29 g).

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with 1N HCl (250 mL), H2O (250 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-134fadaa76494e69ad4d76e6b7e8b8d7
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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