Allyl bromide → HCID 20356329, compound

HRID 371747Notes

Reaction equation

HRID 371747 reaction equation
[C:1]12([CH2:10][NH2:11])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[H-].[Na+].[CH2:14]([Br:17])[CH:15]=[CH2:16]>CN(C)C=O>[BrH:17].[CH2:16]([NH:11][CH2:10][C:1]12[C:7]([CH3:8])([CH3:9])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 20356306HCID 20356306, compound

Product 1

HCID 20356329HCID 20356329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10-bornanamine (1 g.) sodium hydride (0.16 g.) and dimethyl formamide was stirred for 15 min. It was then cooled in an ice bath and allyl bromide (0.55 ml) was added. The mixture was stirred for 2 hours at room temperature and then partitioned between ether and water. The organic layer was dried (MgSO4) and evaporated. The residue (1.04 g.) was subjected to preparative layer chromatography using a mixture of 5% methanol in chloroform for development of the plates. The more polar fraction (0.6 g) was dissolved in dry ether and treated with hydrogen chloride to give 10-allylamino bornane hydrobromide (0.65 g.).

Workup

  1. temperatureIt was then cooled in an ice bath
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. custompartitioned between ether and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. additiona mixture of 5% methanol in chloroform for development of the plates
  7. dissolutionThe more polar fraction (0.6 g) was dissolved in dry ether
  8. additiontreated with hydrogen chloride

Sources & evidence

ORD record
ord-4b1c0afaf8bc4278918cc6c4f744aa8c
Source dataset
uspto-grants-1978_05
Patent number
US04087551

Reaction notes

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