Formic Acid → 1,2,2,4-Tetramethyl decahydroquinoline

HRID 616233Notes

Reaction equation

HRID 616233 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:11][CH:10]([CH3:12])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.[CH:14](O)=O.C=O.[OH-].[Na+]>O.C(OCC)C>[CH3:14][N:3]1[CH:4]2[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:10]([CH3:12])[CH2:11][C:2]1([CH3:13])[CH3:1]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 226287862,2,4-Trimethyldecahydroquinoline

Product 1

HCID 205430951,2,2,4-Tetramethyl decahydroquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

1,2,2,4-tetramethyl decahydroquinoline was prepared. 36.3 grams (0.2 mole) of 2,2,4-trimethyl decahydroquinoline of about 58% cis structure was placed in a reactor vessel equipped for agitation. Formic acid, 20.2 grams (0.44 mole) was added dropwise to the reactor vessel followed by the slow addition of 17.4 grams of 38% by weight formaldehyde in water solution. After addition, the mix was refluxed at for 4 hours. A 5N sodium hydroxide solution was then added until the mix was basic. Diethyl ether was added and the mix separated out and the ether fraction obtained. The fraction was concentrated and then distilled using a 3 inch Vigreaux column to yield 5.4 grams of a product boiling at 70° C. at 0.6 mm Hg. The NMR spectra of the product was consistent with the desired product, 1,2,2,4-tetramethyl decahydroquinoline. The theoretical carbon, hydrogen, nitrogen analysis for the formula C13H25N is 79.92% carbon, 12.90% hydrogen, and 7.17% nitrogen while measured values were 77.23% carbon, 13.13% hydrogen, and 6.56% nitrogen.

Workup

  1. customwas placed in a reactor vessel
  2. customequipped for agitation
  3. additionAfter addition
  4. temperaturethe mix was refluxed at for 4 hours
  5. customthe mix separated out
  6. customthe ether fraction obtained
  7. concentrationThe fraction was concentrated
  8. distillationdistilled

Sources & evidence

ORD record
ord-f6bafa56c6df4eed9a720ddc5e344fe9
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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