Triethylamine → (2,3-Dihydro-1H-inden-2-yl)methanamine

HRID 19721Notes

Reaction equation

HRID 19721 reaction equation
ClC(OCC)=O.[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[CH2:16]C(O)=O.C([N:22](CC)CC)C.[N-]=[N+]=[N-].[Na+]>CC(C)=O.O.[Cl-].[Na+].O>[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[CH2:16][NH2:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Product 1

HCID 22346315(2,3-Dihydro-1H-inden-2-yl)methanamine

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
5 °C

Procedure

Ethyl chloroformate (3.3 ml, 34 mmol) is added to a cooled (0° C.) solution of indan-2-yl acetic acid (5.0 g, 28.4 mmol) and triethylamine (4.75 ml, 34 mmol) in acetone (40 ml) and water (8 ml). After 30 minutes, a solution of sodium azide (2.8 g, 42.6 mmol) in water (16 ml) is added and the reaction is stirred at 5° C. for 1 hour, prior to addition of brine and ice. The mixture is extracted with ether and the combined extracts are dried (Na2SO4) and evaporated. The resultant acyl azide is taken into toluene (50 ml) and heated at 100° C. until nitrogen evolution ceases. After evaporation of solvent, the resultant isocyanate is taken into 6N HCl (40 ml) and heated at 100° C. for 16 hours. The reaction mixture is evaporated to ⅓ volume and the resultant solid collected by filtration, washed with water and ether, then dried. The resultant hydrochloride salt is suspended in ether (20 ml) and ammonia is bubbled for 10 minutes. Water is added and the organic layer is separated, dried (Na2SO4) and evaporated to afford the title compound [MH+CH3CN]+189.

Workup

  1. extractionThe mixture is extracted with ether
  2. dry with materialthe combined extracts are dried (Na2SO4)
  3. customevaporated
  4. temperatureheated at 100° C. until nitrogen evolution ceases
  5. customAfter evaporation of solvent
  6. temperatureheated at 100° C. for 16 hours
  7. customThe reaction mixture is evaporated
  8. filtrationthe resultant solid collected by filtration
  9. washwashed with water and ether
  10. customdried
  11. customammonia is bubbled for 10 minutes
  12. additionWater is added
  13. customthe organic layer is separated
  14. dry with materialdried (Na2SO4)
  15. customevaporated

Sources & evidence

ORD record
ord-1c726865a6314574983d323acc4dc397
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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