Dichloromethane → HCID 22161755, compound

HRID 1088705Notes

Reaction equation

HRID 1088705 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.ClCCl.[OH-].[Na+]>CCOCC>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:15][CH2:14][CH2:13][CH2:12][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 21806145HCID 21806145, compound

Product 1

HCID 22161755HCID 22161755, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-quinolinebutanol (2.56 g), 1,6-dibromohexane (5 ml), dichloromethane (2 ml), TAB (150 mg) and 50% aqueous sodium hydroxide (5 ml) was stirred at room temperature for 18 h. Ether (40 ml) was added and the organic phase separated, washed with water (20 ml), brine (20 ml), dried and evaporated in vacuo to an oil. The oil was purified by chromatography over a column of silica (Merck 60, Art. 7734). Elution with hexane and hexane-ether (9:1) followed by hexane-ether (1:1) afforded the title compound (2.12 g) as a colourless oil, t.l.c. (diethyl ether), Rf 0.50.

Workup

  1. customthe organic phase separated
  2. washwashed with water (20 ml), brine (20 ml)
  3. customdried
  4. customevaporated in vacuo to an oil
  5. customThe oil was purified by chromatography over a column of silica (Merck 60, Art. 7734)
  6. washElution with hexane and hexane-ether (9:1)

Sources & evidence

ORD record
ord-7d29af02366c40a9a8f613e046a1e91a
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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