HCID 53958373, compound → HCID 19981501, compound

HRID 1461144Notes

Reaction equation

HRID 1461144 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:17][CH:18]([N:20]([CH3:22])[CH3:21])[CH3:19])[CH:8]=[CH:9][CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:17][CH:18]([N:20]([CH3:21])[CH3:22])[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 53958373HCID 53958373, compound

Product 1

HCID 19981501HCID 19981501, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.05 g of ethyl 6,6-diphenyl-8-dimethylaminonona-2,4-dienoate was dissolved in toluene (5 ml) and evaporated to dryness twice. The oil was taken up in 95% ethanol (25 ml) and placed in a Paar shaker bottle with 10% palladium on activated carbon (Pd/C, 190 mg). Paar shaker hydrogenation was conducted at room temperature and 60 psi pressure. After 1 hour, an additional 150 mg of catalyst were added and the hydrogenation reaction continued for 3 hours. TLC indicated complete reaction. The catalyst was removed by filtration, and the filtrate was concentrated to dryness to provide 863 mg of ethyl 6,6-diphenyl-8-dimethylaminononanoate, as a clear light yellow oil.

Workup

  1. customevaporated to dryness twice
  2. customwas conducted at room temperature
  3. additionan additional 150 mg of catalyst were added
  4. customthe hydrogenation reaction
  5. waitcontinued for 3 hours
  6. customreaction
  7. customThe catalyst was removed by filtration
  8. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-688e6e241ef449a09e780b5cdd00cf37
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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