Allyl bromide → HCID 11540023, compound

HRID 2181572Notes

Reaction equation

HRID 2181572 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[CH2:8][CH2:7]1)=[O:5].C([O-])([O-])=O.[K+].[K+].C(Br)C=C>CN(C=O)C>[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:19]=[CH:20][C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9]([CH2:12][CH:13]=[CH2:14])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 9890734HCID 9890734, compound

Product 1

HCID 11540023HCID 11540023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of the amine hydrochloride salt of Example 9, part E (4.78 g, 10.8 mmol) in DMF (25 mL) were added K2CO3 (2.98 g, 21.6 mmol) and allyl bromide (0.935 mL, 10.8 mmol), and the solution was stirred for 5 hours at ambient temperature. The solution was partitioned between ethyl acetate and H2O, and the organic layer was washed with H2O and saturated NaCl, and dried over magnesium sulfate. Filtration through a pad of silica (hexane/ethyl acetate) provided the allyl amine as an oil (4.80 g, quantitative yield).

Workup

  1. customThe solution was partitioned between ethyl acetate and H2O
  2. washthe organic layer was washed with H2O and saturated NaCl
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration through a pad of silica (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-24db9ee95a044eaab3dea293dd0c0aeb
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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