Sodium Chloride → HCID 4420058, compound

HRID 2066838Notes

Reaction equation

HRID 2066838 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:10]=1[F:19].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>CN(C=O)C.O>[F:19][C:10]1[CH:11]=[C:12]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:13]=[CH:14][C:9]=1[N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 79341Piperidin-4-olHCID 27827431,2-Difluoro-4-(methylsulfonyl)benzene

Product 1

HCID 4420058HCID 4420058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Hydroxypiperidine (658 mg, 6 5 mmol) and 1,2-difluoro-4-(methanesufonyl)benzene (1.98 g, 5.1 mmol) were combined in DMF (5 mL). Sodium carbonate (705 mg, 6.7 mmol) was added and the mixture was heated at 60 ° C. for 18 h. The mixture was cooled to room temperature and then poured into a mixture of water (10 mL) and a saturated sodium chloride solution (10 mL). The mixture was extracted three times with ethyl acetate (15 mL) and the extracts were combined, washed with brine, dried (MgSO4), and concentrated under vacuum to afford 1.46 g of crude 1a, which was used in the subsequent step without purification: LC-MS 274.1 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted three times with ethyl acetate (15 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-93f75f0835d540e18a86e5965b22c783
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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