Toluene → HCID 11276004, compound

HRID 890610Notes

Reaction equation

HRID 890610 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1([C:13]#[N:14])[CH2:12][CH2:11][C:6]2([O:10]CCO2)[CH2:5][CH2:4]1.C#C.[C:18]1(C)[CH:23]=CC=[CH:20][CH:19]=1>[Co+].C1(C2CCC=CCCC=2)C=CC=C1>[CH3:15][N:2]([CH3:1])[C:3]1([C:13]2[CH:20]=[CH:19][CH:18]=[CH:23][N:14]=2)[CH2:4][CH2:5][C:6](=[O:10])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6326Acetylene2×HCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 11276004HCID 11276004, compound

Reagents, catalysts & solvents 1

HCID 178419946HCID 178419946, compoundCatalyst

Procedure

A solution of 4.5 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, 50 mg cyclopentadienyl cycloocta-1,5-diene cobalt (I) [cpCo(cod)] and 100 ml toluene were transferred into the reaction vessel in a protective gas/acetylene counterflow. After saturation with acetylene the reaction solution was irradiated for a period of 6 hours at a temperature of 25° C. with vigorous stirring. The reaction was interrupted by switching off the lamps and air supply, and the reaction solution was concentrated to low volume. The resulting crude product (5.47 g) was taken up in a mixture of water (8.7 ml) and concentrated hydrochloric acid (15 ml) and stirred overnight at room temperature. To recover the product it was washed with diethyl ether (3×100 ml), the phases separated, the aqueous phase alkalified with 32 percent by mass of sodium hydroxide solution, extracted with dichloromethane (3×100 ml), the combined extracts dried (Na2SO4), filtered and concentrated to low volume. 3.72 g 4-dimethylamino-4-pyridin-2-yl cyclohexanone were obtained.

Workup

  1. concentrationthe reaction solution was concentrated to low volume
  2. additionThe resulting crude product (5.47 g) was taken up in a mixture of water (8.7 ml) and concentrated hydrochloric acid (15 ml)
  3. customTo recover the product it
  4. washwas washed with diethyl ether (3×100 ml)
  5. customthe phases separated
  6. extractionextracted with dichloromethane (3×100 ml)
  7. dry with materialthe combined extracts dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-a621b7943e2048feaeddfc6460819b4b
Source dataset
uspto-grants-2006_02
Patent number
US06998409B2

Reaction notes

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