Hydrochloric Acid → (3-Chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

HRID 1881227Notes

Reaction equation

HRID 1881227 reaction equation
[I-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:7][C:8]1[C:9]2[CH:25]=[C:24]([O:26]C)[C:23]([O:28]C)=[CH:22][C:10]=2[S:11][C:12]=1[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)=[O:14].Cl.[O-]S([O-])=O.[Na+].[Na+]>C(#N)C.O>[Cl:7][C:8]1[C:9]2[CH:25]=[C:24]([OH:26])[C:23]([OH:28])=[CH:22][C:10]=2[S:11][C:12]=1[C:13]([N:15]1[CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]1)=[O:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 6451240Aluminum(III) ChlorideHCID 67094368(3-Chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

Product 1

HCID 67094375(3-Chloro-5,6-dihydroxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Sodium iodide (1.62 g) was added to a solution of aluminum chloride (2.52 g) in acetonitrile (7 ml). After 30 minutes stirring (3-chloro-5,6-dimethoxy-benzo[b]thiophen-2-yl)-(4-hydroxy-piperidin-1-yl)-methanone (0.96 g) was added and the mixture was heated at 50° C. for 12 hours. To the mixture 2 N HCl (4 ml), Na2SO3 (0.68 g) and water were added and the mixture was heated at 60° C. for 30 minutes and then cooled to room temperature. The precipitate was filtered.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated at 60° C. for 30 minutes
  3. temperaturecooled to room temperature
  4. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-281b1fb5b1604a7b9435453814e9d42d
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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