Sodium Iodide → HCID 66879064, compound

HRID 39021Notes

Reaction equation

HRID 39021 reaction equation
[F:1][C:2]1[C:7]2[O:8][C@@H:9]([CH2:12][NH:13][CH2:14][CH3:15])[CH2:10][O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+].[I-]>C(#N)C>[CH2:22]([N:13]([CH2:12][C@@H:9]1[O:8][C:7]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[O:11][CH2:10]1)[CH2:14][CH3:15])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66878480N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine

Product 1

HCID 66879064HCID 66879064, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-{[(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl}ethanamine (1.95 g, 9.2 mmol), K2CO3 (2.55 g, 18.5 mmol), benzylbromide (1.3 ml, 11.1 mmol), a spatula of NaI (<5 mg) and acetonitrile was heated under microwave radiation at 120° C. for 20 min. The solution was filtered and evaporated, Na2CO3 (10%) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) yielded 2.3 g of the title compound. MS m/z (rel. intensity, 70 eV) 149 (10), 148 (86), 92 (8), 91 (bp), 65 (7).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. additionNa2CO3 (10%) was added
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customevaporated to dryness
  7. customPurification on flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record
ord-be9f354597344bb7a8fb2e2c383e592c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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