Sodium Hydroxide → HCID 24260487, compound

HRID 2170508Notes

Reaction equation

HRID 2170508 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[CH2:9][C:10]([NH2:12])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:13])[CH2:9][CH2:10][NH2:12])=[CH:6][CH:7]=1

Participants

5

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-bromophenyl)butanamide (0.60 g, 2.48 mmol) in anhydrous tetrahydrofuran (15 mL) was added Lithium aluminum hydride (0.14 g, 37.2 mmol), the mixture was stirred at reflux for 1.5 hours, after the completion of the reaction, the mixture was cooled to 0° C., 1N sodium hydroxide solution (10 mL) was added slowly, after the reaction, the mixture was stirred at room temperature for 15 minutes. The mixture was filtered and the filtration was collected and extracted with ethyl acetate (10 mL×3), the organic phase was collected and dried over sodium sulfate, removed the solvent under reduce pressure to give 3-(4-bromophenyl)butan-1-amine as a pale yellow oil (0.57 g, 100%) which could be used in the next step without further purification. LR S (M+H+) m/z: calcd for 228.13. found 228.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customafter the completion of the reaction
  3. customafter the reaction
  4. stirringthe mixture was stirred at room temperature for 15 minutes
  5. filtrationThe mixture was filtered
  6. filtrationthe filtration
  7. customwas collected
  8. extractionextracted with ethyl acetate (10 mL×3)
  9. customthe organic phase was collected
  10. dry with materialdried over sodium sulfate
  11. customremoved the solvent

Sources & evidence

ORD record
ord-7fdb1ed3d25f451aa2416c73897c0874
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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