Sodium Carbonate → HCID 53830131, compound

HRID 1934583Notes

Reaction equation

HRID 1934583 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[CH2:8][CH2:9][N:10]1[C:14](=[O:15])[N:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:12]=[N:11]1.[CH3:35][C@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH2:37]>CN1CCCC1=O>[OH:34][C:31]1[CH:32]=[CH:33][C:28]([N:25]2[CH2:26][CH2:27][N:22]([C:19]3[CH:20]=[CH:21][C:16]([N:13]4[CH:12]=[N:11][N:10]([CH2:9][CH2:8][NH:37][C@@H:36]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH3:35])[C:14]4=[O:15])=[CH:17][CH:18]=3)[CH2:23][CH2:24]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6431891-Phenethylamine, (+)-HCID 22466443HCID 22466443, compound

Product 1

HCID 53830131HCID 53830131, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
60 °C

Procedure

Reaction under N2 atmosphere. Na2CO3 (0.01 mol) was added to a mixture of 2-(2-bromoethyl)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H -1,2,4-triazol-3-one (0.0054 mol) in 1-methyl-2-pyrrolidinone (25 ml). This mixture was stirred at 60° C. A solution of (+)-(R)-α-methylbenzenemethanamine (0.0065 mol) in 1-methyl-2-pyrrolidinone (25 ml) was added dropwise and the resulting reaction mixture was stirred overnight at 60° C. The reaction mixture was cooled, poured out into ice-water and the resulting precipitate was filtered off, washed with water, then dried. This fraction was recrystallized from 2-propanol, filtered off and dried, yielding 1.98 g (77%)of (R)-2,4-dihydro4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-[2-[(1-phenylethyl)amino]ethyl]-3H-1,2,4-Triazol-3-one (interm. 19).

Workup

  1. customReaction under N2 atmosphere
  2. customthe resulting reaction mixture
  3. stirringwas stirred overnight at 60° C
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customThis fraction was recrystallized from 2-propanol
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-38eb8d43612e4f8ebbfe126c8d459654
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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