Water → HCID 67126636, compound

HRID 706910Notes

Reaction equation

HRID 706910 reaction equation
[F:1][CH2:2][CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)[CH2:4][F:5].[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28].O>O1CCCC1>[F:5][CH2:4][CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][O:13][C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][C:18]=2[N+:27]([O-:29])=[O:28])[CH2:8][CH2:7]1)[CH2:2][F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 167824874-Fluoro-3-nitrobenzenesulfonamideHCID 67170709HCID 67170709, compound

Product 1

HCID 67126636HCID 67126636, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1-(1,3-difluoropropan-2-yl)piperidin-4-yl)methanol (0.068 g) in tetrahydrofuran (1 mL) was added sodium hydride (0.056 g) and the reaction stirred for 30 minutes at room temperature. 4-Fluoro-3-nitrobenzenesulfonamide (0.077 g) was added in one portion and stirring was continued for 1 hour. The reaction was poured into water (20 mL) and extracted with dichloromethane. The pH of the aqueous layer was adjusted to pH˜8 and it was extracted with dichloromethane (50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to give the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. extractionextracted with dichloromethane
  4. extractionwas extracted with dichloromethane (50 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a05e295364443f982580cb4dc557fa7
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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