Hydrochloric Acid → 6'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 539332Notes

Reaction equation

HRID 539332 reaction equation
Cl.[F:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C:11]1([CH2:20][CH2:19][CH:18]([O:21][CH3:22])[CH2:17][CH2:16]1)[C:10]2=[N:23]S(C(C)(C)C)=O>O1CCOCC1.C([O-])(O)=O.[Na+]>[F:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13]([CH2:12][C:11]3([CH2:16][CH2:17][CH:18]([O:21][CH3:22])[CH2:19][CH2:20]3)[C:10]2=[NH:23])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67979469N-(5'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-yhdene)-2-methylpropane-2-sulfinamide

Product 1

HCID 679795506'-(3-Fluoropropoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imineYield 111.3%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

HCl (4 M in 1,4-dioxane, 1.489 mL, 5.96 mmol) was added to a solution of N-(5′-(3-fluoro-propoxy)-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 20v, Step 1, 244 mg, 0.60 mmol) in anhydrous 1,4-dioxane (25 mL). A white precipitate was formed immediately and the resulting cloudy mixture was stirred under a nitrogen atmosphere overnight. The mixture was diluted with NaHCO3 (aq) and extracted with DCM, dried over MgSO4 and concentrated in vacuo to give 204 mg (quantitative yield) of the title compound that was used without any purification in the next step: MS (ES+) m/z 306 [M+H]+.

Workup

  1. customA white precipitate was formed immediately
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5231571552a4faf9098e9c591663713
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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