Ethanol → HCID 70184421, compound

HRID 370292Notes

Reaction equation

HRID 370292 reaction equation
[CH2:1]([O:3][C:4]([C:6](C)([C:10]([NH:21][CH2:22]C)(C)CC1C=CC=C(OC)C=1)[C:7]([O-:9])=O)=[O:5])[CH3:2].[CH3:25][C:26]([CH3:29])([O-])C.[K+].[CH2:31]([OH:33])C.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[C:4]([CH:6]1[CH2:10][N:21]([CH3:22])[CH:40]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:33][CH3:31])[CH:35]=2)[C:26]([CH3:29])([CH3:25])[C:7]1=[O:9])([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 23665647Potassium tert-butoxideHCID 131722141HCID 131722141, compound

Product 1

HCID 70184421HCID 70184421, compound

Conditions

Temperature
70 °C

Procedure

469.2 g (1.3 mol) of ethyl 3-(2-ethoxycarbonylethyl)amino-4-(3-methoxyphenyl)-2-dimethylbutanoate (5) [R2 =m-CH3O] are dissolved in 7.8 liters of toluene and first about 100 ml of a solvent/water mixture are distilled off. The residue is allowed to cool to about 70° C., mixed with 158.3 g (1.4 mol) of potassium tert.-butoxide and heated to 105° C. for 40 minutes, whilst the ethanol formed is distilled off. It is then cooled to 5 C and mixed with 1.2 liters of ice water and 280 ml of conc. hydrochloric acid. 1.2 liters of ether and 220 ml of conc. ammonia solution are added, the organic phase is separated off and the aqueous phase is extracted twice more with 600 ml of diethylether. The combined organic phases are washed twice with 600 ml of water, dried over sodium sulphate and evaporated down in vacuo. The 5-carbethoxy-3,3-dimethyl-2-(3-methoxyphenyl)-methyl-4-piperidone (6) is isolated in a yield of 390.1 g (95.1% of theory) as a reddish-brown oil.

Workup

  1. distillationfirst about 100 ml of a solvent/water mixture are distilled off
  2. customformed
  3. distillationis distilled off
  4. temperatureIt is then cooled to 5 C
  5. additionmixed with 1.2 liters of ice water and 280 ml of conc. hydrochloric acid
  6. addition1.2 liters of ether and 220 ml of conc. ammonia solution are added
  7. customthe organic phase is separated off
  8. extractionthe aqueous phase is extracted twice more with 600 ml of diethylether
  9. washThe combined organic phases are washed twice with 600 ml of water
  10. dry with materialdried over sodium sulphate
  11. customevaporated down in vacuo

Sources & evidence

ORD record
ord-d41bb63615714bd8b0fee4b3ee9da93c
Source dataset
uspto-grants-2000_10
Patent number
US06140502

Reaction notes

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