Triethylamine → HCID 54276261, compound

HRID 1585543Notes

Reaction equation

HRID 1585543 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([OH:8])=O.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27][C@@H:28]2[CH2:33][NH:32][C:31](=[O:34])[CH2:30][NH:29]2)=[CH:19]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl.O>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:29]1[C@H:28]([CH2:27][C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:18][CH:19]=2)[CH2:33][NH:32][C:31](=[O:34])[CH2:30]1)=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 54357522HCID 54357522, compound

Product 1

HCID 54276261HCID 54276261, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,5-bis(trifluoromethyl)benzoic acid (2.63 g) and (5R)-5-(1H-indol-3-ylmethyl)piperazin-2-one (2.34 g) in dichloromethane (50 ml) were added successively triethylamine (3.56 ml) and 2-chloro-1-methylpyridinium iodide (3.13 g) at room temperature. The resulting mixture was stirred for 1.5 hours at the same temperature. Dichloromethane and water were added into the mixture and the organic layer was separated. The organic layer was washed successively with 0.5N hydrochloric acid, water, aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (75 g) eluting with a mixture of dichloromethane-methanol (from 0% to 5% gradient elution) to give (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-5-(1H-indol-3-ylmethyl)piperazin-2-one (1.25 g) as an oil.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed successively with 0.5N hydrochloric acid, water, aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation in vacuo
  5. customthe residue was purified by column chromatography on silica gel (75 g)
  6. washeluting with a mixture of dichloromethane-methanol (from 0% to 5% gradient elution)

Sources & evidence

ORD record
ord-e4b2dc97885243b4a572335cc7ef6c33
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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