Hydrochloric Acid → 4-(1H-Indol-3-YL)cyclohexanone

HRID 1250152Notes

Reaction equation

HRID 1250152 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 108487533-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indole

Product 1

HCID 108462644-(1H-Indol-3-YL)cyclohexanoneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 23° C. solution of 8.66 g (33.7 mmol) 3-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-indole and 200 mL THF was added 200 mL of 1N HCl. After stirring for 12 h, the organics were evaporated and the resulting slurry was extracted with 2×150 mL EtOAc. The combined organics were washed with 2×100 mL of 1N NaOH, dried over MgSO4, filtered and evaporated to an off-white solid. Flash chromatography on silica gel, eluting with hexanes/EtOAc (1/1) gave 5.89 g (27.6 mmol, an 82% yield) of the title compound as a white solid. mp 123-125° C.; MS (ES) m/z (relative intensity): 214 (M++H, 100.

Workup

  1. customthe organics were evaporated
  2. extractionthe resulting slurry was extracted with 2×150 mL EtOAc
  3. washThe combined organics were washed with 2×100 mL of 1N NaOH
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an off-white solid
  7. washFlash chromatography on silica gel, eluting with hexanes/EtOAc (1/1)
  8. customgave 5.89 g (27.6 mmol

Sources & evidence

ORD record
ord-1289fb62bebc4f7fbc481c087fff3f13
Source dataset
uspto-grants-2002_01
Patent number
US06337326B1

Reaction notes

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