Acetonitrile → 2-[4-[(6-Bromohexyl)oxy]butyl]-N,N-diethylbenzamide

HRID 1721912Notes

Reaction equation

HRID 1721912 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[CH:12].[CH2:13]([N:15]([CH2:25][CH3:26])[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1I)[CH3:14].C1(NC2CCCCC2)CCCCC1.C(#N)C>CCOCC.[Cu]I>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:16]([N:15]([CH2:13][CH3:14])[CH2:25][CH3:26])=[O:24]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7582DicyclohexylamineHCID 789049N,N-Diethyl-2-iodobenzamideHCID 113792816-Bromohexylbut-3-ynyl ether

Product 1

HCID 200298332-[4-[(6-Bromohexyl)oxy]butyl]-N,N-diethylbenzamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of CuI (20 mg), 1-bromo-6-[(3-butynyl)oxyl]hexane (3.04 g), N,N-diethyl-2-iodobenzamide (3.95 G), BTPC (200 mg), N,N-dicyclohexylamine (2.60 g) and acetonitrile (20 ml) was stirred under nitrogen at room temperature for 4.5 h, diluted with ether (200 ml) and filtered. The filtrate was evaporated in vacuo, the residue in ethanol (100 ml) was treated with charcoal and the solvent evaporated in vacuo. The residual oil (5.32 g) in absolute ethanol (190 ml) was hydrogenated over pre-reduced 10% PDO-C (50% paste in water, 1.25 g) in absolute ethanol (20 ml), filtered through hyflo and evaporated in vacuo to give an oil. Purification by FCC eluting with T-EA-triethylamine (95:5:1) followed by FCC eluting with CX-EA (2:1) gave the title compound as a yellow oil (2.04 g). T.l.c. (T-ET-A-40:10:1) Rf 0.14.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. additionthe residue in ethanol (100 ml) was treated with charcoal
  4. customthe solvent evaporated in vacuo
  5. filtrationfiltered through hyflo
  6. customevaporated in vacuo
  7. customto give an oil
  8. customPurification by FCC
  9. washeluting with T-EA-triethylamine (95:5:1)
  10. washeluting with CX-EA (2:1)

Sources & evidence

ORD record
ord-a827614f267048adb2b2ab770030ac75
Source dataset
uspto-grants-1989_08
Patent number
US04853382

Reaction notes

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