Potassium Carbonate → 2-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-7-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepin-5-one 1,1-dioxide

HRID 649761Notes

Reaction equation

HRID 649761 reaction equation
[CH3:1][N:2]1[CH:11]=[C:10]2[C:4]([C:5](=[O:14])[CH2:6][CH2:7][NH:8][S:9]2(=[O:13])=[O:12])=[CH:3]1.Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:31][C:28]1[CH:27]=[CH:26][C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][N:8]3[CH2:7][CH2:6][C:5](=[O:14])[C:4]4=[CH:3][N:2]([CH3:1])[CH:11]=[C:10]4[S:9]3(=[O:13])=[O:12])[CH2:24][CH2:23]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazineHCID 220659017-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepin-5-one 1,1-dioxide

Product 1

HCID 99107952-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-7-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepin-5-one 1,1-dioxideYield 58%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 236 mg (1.1 mmol) of Compound 15, 308 mg (1.2 mmol) of 1-(3-chloropropyl)-4-(4-fluoro-phenyl)piperazine and 304 mg (2.2 mmol) of potassium carbonate in 15 ml of 2-butanone was refluxed for 16 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: ethyl acetate), whereby 276 mg of the title compound were obtained (yield: 58%).

Workup

  1. temperaturewas refluxed for 16 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: ethyl acetate)

Sources & evidence

ORD record
ord-0d3ab51a66484aa292885ab82ece1ecb
Source dataset
uspto-grants-2001_08
Patent number
US06271223B1

Reaction notes

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