1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(3-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propylsulfonyl)-4-(1-methylpiperidin-4-yl)piperazine

HRID 1643461Notes

Reaction equation

HRID 1643461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22]([O:25]C2C(F)=C(F)C(F)=C(F)C=2F)(=O)=[O:23])(=[O:12])=[O:11])=[C:5]([CH3:37])[CH:4]=1.[CH3:38][N:39]1[CH2:44][CH2:43][CH:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH2:41][CH2:40]1.N12CCCN=C1CCCCC2.C(=O)(O)[O-].[Na+]>O1CCCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:37])[C:6]([S:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH2:21][S:22]([N:48]2[CH2:47][CH2:46][N:45]([CH:42]3[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]3)[CH2:50][CH2:49]2)(=[O:23])=[O:25])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 59367793Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate

Product 1

HCID 593677251-(3-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propylsulfonyl)-4-(1-methylpiperidin-4-yl)piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Perfluorophenyl 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonate (40 mg, 0.07 mmol) and 1-(1-methyl-4-piperidinyl)piperazine (25 mg, 0.14 mmol) were dissolved in tetrahydrofuran (10 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.03 ml, 0.21 mmol) was added under an inert gas and the mixture was refluxed for 1 h and stirred at room temperature for 15 h. Methylene chloride and saturated sodium bicarbonate solution (10 ml of each) were added, the phases were separated and the aqueous phases were extracted with methylene chloride (20 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25 aq) (200:100:1). Yield: 18 mg (45%). MS, m/z=571.3 [MH]+

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customthe phases were separated
  3. extractionthe aqueous phases were extracted with methylene chloride (20 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25 aq) (200:100:1)

Sources & evidence

ORD record
ord-c21699cf1e1847769e1f381d4521bfb5
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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