Sodium Chloride → HCID 86751312, compound

HRID 1379207Notes

Reaction equation

HRID 1379207 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15]Cl)[CH2:10][C@H:9]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:7].[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.[K].[Cl-].[Na+]>CN(C)C=O>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH2:15][N:41]2[C:40](=[O:42])[C:39]3=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]3[C:37]2=[O:47])=[O:17])[CH2:10][C@H:9]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:7]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24194345Phthalimide potassium saltHCID 86751318HCID 86751318, compound

Product 1

HCID 86751312HCID 86751312, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(2-chloroacetyl)-2-(1H-indol-3-yl-methyl)piperazine (730 mg), potassium phthalimide (260 mg) in dimethylformamide (10 ml) was stirred at room temperature for 7 hours and then poured into aqueous sodium chloride solution (100 ml). The resulting precipitate was collected by filtration, washed with water and dried. The crude product was dissolved in toluene (7 ml) and filtered. To the filtrate was added n-hexane (35 ml) and the whole was stirred for 10 minutes. The resulting powder was collected by filtration, washed with ethyl ether and dried to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(phthalimidomethylcarbonyl)piperazine (500 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. dissolutionThe crude product was dissolved in toluene (7 ml)
  5. filtrationfiltered
  6. additionTo the filtrate was added n-hexane (35 ml)
  7. stirringthe whole was stirred for 10 minutes
  8. filtrationThe resulting powder was collected by filtration
  9. washwashed with ethyl ether
  10. customdried

Sources & evidence

ORD record
ord-8e4cc5bf32fa462bbf7823f9b20cb2e9
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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