Diethyl Ether → HCID 20543100, compound

HRID 616243Notes

Reaction equation

HRID 616243 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:13]2[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:7]([CH3:14])[CH2:6][C:5]1([CH3:16])[CH3:15].[C-:17]#[N:18].[Na+].C(OCC)C>CS(C)=O>[C:17]([CH2:2][CH2:3][N:4]1[CH:13]2[CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:7]([CH3:14])[CH2:6][C:5]1([CH3:16])[CH3:15])#[N:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 205430821-(2-Chloroethyl)-2,2,4-trimethyldecahydroquinoline

Product 1

HCID 20543100HCID 20543100, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
95 °C

Procedure

1-(2'-cyanoethyl)-2,2,4-trimethyl decahydroquinoline was prepared via the post-reaction of the above chloroethyl substituted compound. 61.0 grams (0.25 mole) of 1-(2'-chloroethyl)-2,2,4-trimethyl decahydroquinoline dissolved in 50 milliliters of methyl sulfoxide was added dropwise over a period of 40 minutes at room temperature to a prepared solution of 12.25 grams (0.25 mole) of sodium cyanide in 150 milliliters of methyl sulfoxide. The mix was then heated to 95° C. and stirred for 2.5 hours. The reaction mixture was then cooled, poured into 500 milliliters of ice water, diethyl ether was added, the organic layer separated out. The aqueous layer was washed with four 100 milliliter portions of diethyl ether and the ether washes combined wih the original organic layer. The solution was then concentrated and distilled using a 6 inch Vigreaux column to yield 43.0 grams of a liquid product boiling at 134° - 136° C. at 3.3 mm Hg. The infrared spectrum of the product is consistent with the desired compound, 1-(2'-cyanoethyl)-2,2,4-trimethyl decahydroquinoline. Calculated values for the formula C15H26N2 are 76.87% carbon, 11.18% hydrogen, and 11.95% nitrogen and found contents were 76.71% carbon, 11.02% hydrogen, and 11.15% nitrogen.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionwas added
  3. customthe organic layer separated out
  4. washThe aqueous layer was washed with four 100 milliliter portions of diethyl ether
  5. concentrationThe solution was then concentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-6e9c6944b8cb4227b922c74374f9b10a
Source dataset
uspto-grants-1978_02
Patent number
US04073770

Reaction notes

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