3-Pyridinemethanol → HCID 66847852, compound

HRID 517004Notes

Reaction equation

HRID 517004 reaction equation
ClC[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][OH:31])[CH:25]=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[S:11]([N:8]1[CH2:7][CH2:6][N:5]([C:3]([O:31][CH2:30][C:26]2[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=2)=[O:4])[CH2:10][CH2:9]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 94429TriphosgeneHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 66847852HCID 66847852, compoundYield 30.27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 4, 0.250 g, 0.905 mmol) and pyridin-3-yl-methanol (98 mg, 0.905 mmol) taken in dry DCM (10 mL), triphosgene (294 mg, 0.99 mmol) was added at 0° C. and allowed to stir at room temperature for 3 h. The mixture was then diluted with DCM washed with water (2×10 mL) & brine (2×10 mL). The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to yield the title compound (0.109 g, 30.27%) as a solid.

Workup

  1. washwashed with water (2×10 mL) & brine (2×10 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-8329713707424dada5fab39208631cc4
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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