Sodium Carbonate → HCID 54024604, compound

HRID 2288188Notes

Reaction equation

HRID 2288188 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]OS(C)(=O)=O)[CH2:10][C@H:9]1[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7].Cl.[C:42]([C:44]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)#[N:43].C(=O)([O-])[O-].[Na+].[Na+]>CO>[F:37][C:35]([F:36])([F:38])[C:33]1[CH:32]=[C:5]([CH:4]=[C:3]([C:2]([F:39])([F:40])[F:1])[CH:34]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:47]2[CH2:48][CH2:49][C:44]([C:42]#[N:43])([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:45][CH2:46]2)[CH2:10][C@H:9]1[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochlorideHCID 53774435HCID 53774435, compound

Product 1

HCID 54024604HCID 54024604, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-methylsulfonyloxypropyl)piperazine (150 mg) and 4-cyano-4-phenylpiperidine hydrochloride (70 mg) in methanol (5 ml) was stirred at reflux temperature in the presence of sodium carbonate (100 mg). After 2 hours, the reaction mixture was evaporated under reduced pressure. The residue was extracted with ethyl acetate and the extract was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-methanol (10:1) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[3-(4-cyano-4-phenylpiperidino)propyl]-2-(1H-indol-3-ylmethyl)piperazine (89 mg) as a powder.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. concentrationthe extract was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0325ca5164d84a3ebb132e6a805308e2
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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