4'-Bromoacetanilide → N-[4-[2-(dimethylamino)-2-methyl-1-oxopropyl]phenyl]acetamide

HRID 1019067Notes

Reaction equation

HRID 1019067 reaction equation
C([Li])(CC)C.Br[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1.[C:17]([C:19]([CH3:24])([N:21]([CH3:23])[CH3:22])[CH3:20])#N.C1C[O:28]CC1>>[CH3:22][N:21]([CH3:23])[C:19]([CH3:24])([CH3:20])[C:17]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)=[O:28]

Participants

5

Reactant 4

HCID 76834'-BromoacetanilideHCID 8028Tetrahydrofuran2×HCID 105108312-(Dimethylamino)-2-methylpropanenitrileHCID 178418400CID 53628100

Product 1

HCID 22603032N-[4-[2-(dimethylamino)-2-methyl-1-oxopropyl]phenyl]acetamideYield 36%

Conditions

Temperature
-70 °C

Procedure

Sec butyllithium (298 ml: 1.3 M) was added dropwise at −60° C. under N2 flow to a solution of N-(4-bromophenyl)acetamide (0.1892 mol) in THF (400 ml) and the mixture was stirred at −70° C. for 2 hours. A solution of 1-cyano-1-methyl-N,N-di-methylethanamine (0.075 mol) in THF (60 ml) was added dropwise, the mixture was brought to RT and then stirred at RT for 12 hours. The mixture was poured into ice and extracted with EtOAc. The solvent was evaporated, the residue was taken up in HCl (3 N) and EtOAc, extracted with EtOAc, basified with K2CO3 (10%) and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was recrystallized from (C2H5)2O and DIPE. The precipitate was filtered off and dried, yielding 6.8 g (36%) of N-[4-[2-(dimethylamino)-2-methyl-1-oxopropyl]phenyl]acetamide (interm. 3).

Workup

  1. customwas brought to RT
  2. stirringstirred at RT for 12 hours
  3. additionThe mixture was poured into ice
  4. extractionextracted with EtOAc
  5. customThe solvent was evaporated
  6. extractionEtOAc, extracted with EtOAc
  7. extractionextracted with CH2Cl2
  8. customThe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. customThe residue was recrystallized from (C2H5)2O and DIPE
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-4abf1ff902194525913aa2663fdd2baf
Source dataset
uspto-grants-2002_11
Patent number
US06486187B1

Reaction notes

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