Sodium Bicarbonate → 4-(5-Cyano-1-methyl-3-indolyl)cyclohexanone

HRID 428511Notes

Reaction equation

HRID 428511 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=4)[N:13]([CH3:22])[CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.C(=O)(O)[O-].[Na+]>O1CCCC1.Cl>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:22])[CH:12]=[C:11]2[CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)#[N:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 184140773-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole

Product 1

HCID 154812824-(5-Cyano-1-methyl-3-indolyl)cyclohexanoneYield 44%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 3-(1,4-dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole (5.5 g) in 150 ml (1:1) tetrahydrofuran-hydrochloric acid (1N) was allowed to stir at room temperature for 16 hours, followed by the addition of 4.49 g sodium bicarbonate. The mixture was extracted with methylene chloride (3×100 ml), washed with brine (3×150 ml). The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed to afford a light brown solid which was boiled in ethyl acetate-hexanes (1:1). The mixture was cooled to room temperature and solid was collected and dried under vacuum to afford 2.06 g of the title compound as a solid: mp 150-152° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride (3×100 ml)
  2. washwashed with brine (3×150 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customto afford a light brown solid which
  7. temperatureThe mixture was cooled to room temperature
  8. customsolid was collected
  9. customdried under vacuum

Sources & evidence

ORD record
ord-5c1db748c3e84421ae1328b084506104
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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