Potassium Carbonate → 5-[3-[4-(4-Fluorophenyl)piperazin-1-yl]propyl]-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide

HRID 351978Notes

Reaction equation

HRID 351978 reaction equation
[CH3:1][N:2]1[CH2:7][C:6](=[O:8])[C:5]2[NH:9][CH:10]=[CH:11][C:4]=2[S:3]1(=[O:13])=[O:12].Cl[CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:30][C:27]1[CH:26]=[CH:25][C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][CH2:15][N:9]3[C:5]4[C:6](=[O:8])[CH2:7][N:2]([CH3:1])[S:3](=[O:13])(=[O:12])[C:4]=4[CH:11]=[CH:10]3)[CH2:23][CH2:22]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazineHCID 155506602-Methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide

Product 1

HCID 99100415-[3-[4-(4-Fluorophenyl)piperazin-1-yl]propyl]-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxideYield 80%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 200 mg (1 mmol) of Compound 12, 385 mg (1.5 mmol) of 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine and 207 mg (1.5 mmol) of potassium carbonate in 15 ml of 2-butanone was refluxed for 24 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: chloroform), whereby 335 mg of the title compound were obtained (yield: 80%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluent: chloroform)

Sources & evidence

ORD record
ord-728b8cbd0cab45cb94c6997434e9250f
Source dataset
uspto-grants-2004_06
Patent number
US06743913B2

Reaction notes

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