Isopropyl iodide → HCID 3054985, compound

HRID 2057934Notes

Reaction equation

HRID 2057934 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][NH:11][CH2:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[CH:17](I)([CH3:19])[CH3:18]>[Ag]=O.CC(C)=O>[CH:17]([N:11]1[CH2:12][CH2:13][CH:14]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[CH2:10]1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 6362Isopropyl iodide2×HCID 3054981HCID 3054981, compound

Product 1

HCID 3054985HCID 3054985, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst2×HCID 180AcetoneSolvent

Procedure

A mixture of 2.2 g of 3-(3-trifluoromethyl-phenyl)-1,2,5,6-tetrahydropyridine, 18 ml of acetone, 1.18 g of silver oxide and 1.4 ml of isopropyl iodide was stirred for 12 hours at room temperature and after the addition of 0.7 ml of isopropyl iodide and 0.5 g of silver oxide, the mixture was stirred another 3 hours at room temperature and was filtered. The filtrate was evaporated to dryness to obtain 2.9 g of raw product which was chromatographed over silica gel. Elution with an 85-10-5 cyclohexane-chloroform-triethylamine mixture yielded 2.21 g of 1-isopropyl-3-(3-trifluoromethyl-phenyl)-1,2,5,6-tetrahydropyridine in the form of a yellow oil.

Workup

  1. stirringthe mixture was stirred another 3 hours at room temperature
  2. filtrationwas filtered
  3. customThe filtrate was evaporated to dryness
  4. customto obtain 2.9 g of raw product which
  5. customwas chromatographed over silica gel
  6. washElution with an 85-10-5 cyclohexane-chloroform-triethylamine mixture

Sources & evidence

ORD record
ord-b55fdb41781246d5afb8128044875559
Source dataset
uspto-grants-1980_07
Patent number
US04213989

Reaction notes

Loading…