Dicyclohexylamine → 2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinoline

HRID 1088714Notes

Reaction equation

HRID 1088714 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25].C1(NC2CCCCC2)CCCCC1>C(#N)C.CCOCC.[Cu]I>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[C:25][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 3

HCID 7582DicyclohexylamineHCID 27627562-BromoquinolineHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Product 1

HCID 198767592-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinolineYield 75.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromoquinoline (3.00 g), 6-[(6-bromohexyl)oxy]-1-hexyne (3.77 g), BTPC (90 mg), copper (I) iodide (11 mg), and dicyclohexylamine (2.79 g) in acetonitrile (35 ml) was stirred at room temperature under nitrogen for 20 h. The mixture was diluted with ether (90 ml), filtered and the filtrate evaporated in vacuo to give a brown oil. Purification by FCC eluting with hexane:ether (4:1→2:1) gave the title compound as a brown oil (4.25 g), t.l.c. (hexane:ether 2:1) Rf 0.22.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customto give a brown oil
  4. customPurification by FCC
  5. washeluting with hexane:ether (4:1→2:1)

Sources & evidence

ORD record
ord-b436ca20d21e4881a68cd55a33b311af
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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