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Water → 2,3-Dihydro-1-benzofuran-7-ylmethylamine

HRID 1034983
Notes
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Reaction equation

HRID 1034983 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[N+]=[N-].[Li].O.[OH-].[Na+]>O1CCCC1>[O:12]1[C:13]2[C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:10][CH2:11]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3028194LithiumHCID 86082286HCID 86082286, compound

Product 1

HCID 235128322,3-Dihydro-1-benzofuran-7-ylmethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Conditions

Temperature
0 °C

Procedure

The product of Example 48C (2.2 g) in tetrahydrofuran (10 mL) was treated with lithium aluminumhydride (0.71 g) in tetrahydrofuran (20 mL) at 0° C. dropwise. The mixture was stirred at 0° C. for 90 minutes then carefully treated in succession with water (0.7 mL), 15% sodium hydroxide (0.7 mL) and water (2.1 mL). After stirring overnight, the mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (70 mL), and the filtrate concentrated under reduced pressure. The crude was dissolved in diethylether, washed with water, and extracted with 1N hydrochloric acid (2×20 mL). The acidic extracts were combined, basified with potassium carbonate, and extracted with methylene chloride (4×). The organic extracts were combined, dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (DCI/NH3) m/z 150 (M+H)+;

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe mixture was filtered through celite
  3. washthe filter cake was washed with tetrahydrofuran (70 mL)
  4. concentrationthe filtrate concentrated under reduced pressure
  5. dissolutionThe crude was dissolved in diethylether
  6. washwashed with water
  7. extractionextracted with 1N hydrochloric acid (2×20 mL)
  8. extractionextracted with methylene chloride (4×)
  9. dry with materialdried (potassium carbonate)
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ea2b3dbd9594552999cd3ab2d24a97f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546374B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes