1-Bromohexane → HCID 20478679, compound

HRID 904761Notes

Reaction equation

HRID 904761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:15]=[C:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:23](Br)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C=O>[CH2:23]([N:12]1[C:11](=[O:20])[CH2:10][C:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:14](=[CH:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 132819714a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Product 1

HCID 20478679HCID 20478679, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The procedure in Example 9, Part A, was followed in which 4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (12 g, 0.05 moles) in 150 ml of anhydrous dimethylformamide was added to a 55% suspension of sodium hydride in mineral oil (2.4 g) in 100 ml of dimethylformamide at 70°; n-hexyl bromide (9.1 g) was added, the reaction heated at 70° for 18 hrs. The crude material obtained from this procedure was chromatographed to yield 12 g of product.

Workup

  1. temperaturethe reaction heated at 70° for 18 hrs
  2. customThe crude material obtained from this procedure
  3. customwas chromatographed

Sources & evidence

ORD record
ord-49e975381e33418ab067667e9b2d5fce
Source dataset
uspto-grants-1983_12
Patent number
US04419517

Reaction notes

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