Hydrochloric Acid → HCID 21562198, compound

HRID 1580541Notes

Reaction equation

HRID 1580541 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH3:10][C:11]1([CH3:20])[NH:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:13](=[O:14])[CH2:12]1.C([Li])CCC.Cl>CCCCCC.CCOCC>[OH:8][CH:7]([CH:15]1[C:13](=[O:14])[CH2:12][C:11]([CH3:20])([CH3:10])[NH:17][C:16]1([CH3:19])[CH3:18])[C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 132202,2,6,6-Tetramethyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 21562198HCID 21562198, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a mixture of 12g. of p-tolualdehyde, 15.5 g. of triacetone amine and 50 ml. of anhydrous ether was added dropwise 42.6g. of butyl lithium (as a 15% solution in n-hexane) at -50° to -60°C. under a nitrogen gas stream. After completion of the dropwise addition, the mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was poured into 5% dilute hydrochloric acid with ice-cooling. The aqueous layer was separated and saturated with potassium carbonate. Then, the ether layer was separated and concentrated to yield crude crystalline mass. The mass was recrystallized from benzene to give the desired product as white crystals having a decomposition point of 160° - 161°C.

Workup

  1. customat -50° to -60°C.
  2. additionAfter completion of the dropwise addition
  3. temperaturecooling
  4. customThe aqueous layer was separated and saturated with potassium carbonate
  5. customThen, the ether layer was separated
  6. concentrationconcentrated
  7. customto yield crude crystalline mass
  8. customThe mass was recrystallized from benzene

Sources & evidence

ORD record
ord-5516064907b8436880a5f3e504fefb09
Source dataset
uspto-grants-1976_01
Patent number
US03933735

Reaction notes

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