Sulfuryl chloride → HCID 68580435, compound

HRID 2233415Notes

Reaction equation

HRID 2233415 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.[O:21]=[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([S:32](Cl)(=[O:34])=[O:33])=[CH:24][NH:23]1.S(Cl)(Cl)(=O)=O>N1C=CC=CC=1>[C:12]([OH:21])(=[O:11])[CH3:17].[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[O:11][CH:8]1[CH2:9][CH2:10][N:5]([CH2:4][C@H:3]([OH:20])[CH2:2][NH:1][S:32]([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22](=[O:21])[NH:23][CH:24]=2)(=[O:33])=[O:34])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-olHCID 86598072HCID 86598072, compound

Product 1

HCID 68580435HCID 68580435, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2R)-1-Amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.1 g) in pyridine (2 ml) was treated with 1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride (0.11 g) and the mixture was stirred at ambient temperature for 18 h. After further additions of the sulfonyl chloride (0.05 g) and stirring for 24 h the solvent was evaporated. Purification by column chromatography and reverse phase HPLC (symmetry C8 column and acetonitrile/0.1% aqueous ammonium acetate) yielded the title compound as a white solid (0.06 g).

Workup

  1. customwas evaporated
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-fbf1906d40844ef3910e3911cbaf970f
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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