Potassium Iodide → HCID 86584249, compound

HRID 2288216Notes

Reaction equation

HRID 2288216 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7].[ClH:34].[S:35]1[CH2:40][CH2:39][N:38]([CH2:41][C:42]#[C:43][CH2:44][Cl:45])[CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[ClH:45].[ClH:34].[F:31][C:28]([F:29])([F:30])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:27]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:44][C:43]#[C:42][CH2:41][N:38]2[CH2:39][CH2:40][S:35][CH2:36][CH2:37]2)[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18703357HCID 18703357, compoundHCID 54095749HCID 54095749, compound

Product 1

HCID 86584249HCID 86584249, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)piperazine (300 mg), 4-thiomorpholino-2-butynyl chloride hydrochloride (170 mg) and powdered potassium carbonate (210 mg) in dry acetonitrile (3 ml) was refluxed for 7.5 hours in the presence of potassium iodide (20 mg). The reaction mixture was cooled and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and methanol (50:1). The obtained product was dissolved in ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate solution (0.6 ml) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(2-naphthylmethyl)-4-(4-thiomorpholino-2-butynyl)piperazine dihydrochloride (300 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by column chromatography on silica gel using
  5. additiona mixture of ethyl acetate and methanol (50:1)
  6. dissolutionThe obtained product was dissolved in ethyl acetate
  7. additiontreated with 4N hydrogen chloride in ethyl acetate solution (0.6 ml)

Sources & evidence

ORD record
ord-69b0edf175a84a399ddcd9fa84518a1f
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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