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

HRID 1886032Notes

Reaction equation

HRID 1886032 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-4e36df1b6661457aa2f85e086e71baf7
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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