Lithium Chloride → HCID 22390426, compound

HRID 1071933Notes

Reaction equation

HRID 1071933 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[CH3:11][C:12]1([CH3:33])[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21](OS(C(F)(F)F)(=O)=O)=[CH:20][C:19]=2[Cl:32])[CH2:14][CH2:13]1.[Cl-].[Li+]>C(N(CC)CC)C.N1C=CC=CC=1.C(OCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[ClH:32].[CH3:11][C:12]1([CH3:33])[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([C:3]#[C:2][CH2:1][N:4]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[CH:20][C:19]=2[Cl:32])[CH2:14][CH2:13]1

Participants

9

Reactant 3

HCID 433294Lithium ChlorideHCID 1268882153678-66-32×HCID 22390465HCID 22390465, compound

Product 1

HCID 22390426HCID 22390426, compound

Reagents, catalysts & solvents 5

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

0.76 g of dichlorobis(triphenylphosphine)palladium are added, under an inert atmosphere, to 3.6 g of 1-prop-2-ynylazepane (compound 4.1), 8 g of [4-(4,4-dimethylcyclohexyl)-3-chlorophenyl]trifluoromethanesulphonate (compound III.1), 0.103 g of copper iodide, 1.83 g of lithium chloride in 200 ml of triethylamine and 100 ml of pyridine. The reaction mixture is heated at reflux for 12 hours. The solvents are evaporated off under reduced pressure and the residue obtained is purified by chromatography on a column of silica gel, eluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture. The residue obtained is taken up in diethyl ether and the hydrochloride is formed by bubbling hydrochloric acid through. After filtration, the residue obtained is recrystallized from toluene.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 hours
  3. customThe solvents are evaporated off under reduced pressure
  4. customthe residue obtained
  5. customis purified by chromatography on a column of silica gel
  6. washeluting with a 95/5 (v/v) cyclohexane/ethyl acetate mixture
  7. customThe residue obtained

Sources & evidence

ORD record
ord-659b69691fd44d47b5affa234479046f
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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