3-Cyanobenzene-1-sulfonyl chloride → HCID 59296073, compound

HRID 2233414Notes

Reaction equation

HRID 2233414 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:20])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:7][CH2:6]1.[C:21]([C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)#[N:22]>N1C=CC=CC=1>[C:21]([C:23]1[CH:24]=[C:25]([S:29]([NH:1][CH2:2][C@@H:3]([OH:20])[CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=3)[CH2:7][CH2:6]2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1)#[N:22]

Participants

4

Reactant 2

HCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Product 1

HCID 59296073HCID 59296073, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2-R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.200 g, 0.63 mmol) in 4 ml of pyridine at 0° C. was added 3-cyanobenzenesulfonyl chloride (0.127 g, 0.63 mmol). After 30 min, the reaction was allowed to warm to room temperature and was stirred for 2 h. The reaction was concentrated under vacuum, and the residue partitioned between 10% aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was washed with water, then brine and dried over magnesium sulfate. The crude material was purified on silica gel (0 to 5% 7N ammonia in methanol/dichloromethane) to afford the title compound as a white foam (0.120 g).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue partitioned between 10% aqueous sodium hydrogen carbonate and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine and dried over magnesium sulfate
  5. customThe crude material was purified on silica gel (0 to 5% 7N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-aa5352ad1a14476c89a3105b938b2146
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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