Methylamine → 5-(3-Amino-4-chlorophenyl)-5-hydroxy-1-methylpyrrolidin-2-one

HRID 231831Notes

Reaction equation

HRID 231831 reaction equation
ClC(OCC)=O.[NH2:7][C:8]1[CH:9]=[C:10]([C:15](=[O:21])[CH2:16][CH2:17][C:18](O)=[O:19])[CH:11]=[CH:12][C:13]=1[Cl:14].[CH2:22]([N:24](CC)CC)C.CN>O1CCCC1>[NH2:7][C:8]1[CH:9]=[C:10]([C:15]2([OH:21])[N:24]([CH3:22])[C:18](=[O:19])[CH2:17][CH2:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 142568023-(3-Amino-4-chlorobenzoyl)propionic acid

Product 1

HCID 142568035-(3-Amino-4-chlorophenyl)-5-hydroxy-1-methylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

42.8 g of ethyl chloroformate are metered into a solution of 60 g of 4-(3-amino-4-chlorophenyl)-4-oxobutyric acid and 27.8 g of triethylamine in 500 ml of tetrahydrofuran in such a way that the temperature does not exceed 10° C. The mixture is stirred in the icebath for a further 10 min and then, while maintaining the cooling, a solution of 35 g of gaseous methylamine in 250 ml of tetrahydrofuran is added, during which a temperature of 25° C. should not be exceeded. After stirring for a further 45 minutes in the icebath, the solvent is removed by distillation, water is added to the residue, and the crystalline precipitate is filtered off. Crystals of melting point 154° C. (from ethanol).

Workup

  1. customdoes not exceed 10° C
  2. temperaturewhile maintaining the cooling
  3. stirringAfter stirring for a further 45 minutes in the icebath
  4. customthe solvent is removed by distillation, water
  5. additionis added to the residue
  6. filtrationthe crystalline precipitate is filtered off

Sources & evidence

ORD record
ord-d0e5d596fc884df5928b712016eebbfd
Source dataset
uspto-grants-1989_07
Patent number
US04849444

Reaction notes

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