Propylamine → N-propyl-2,3-dihydro-1H-inden-2-amine

HRID 1683888Notes

Reaction equation

HRID 1683888 reaction equation
O1CCCC1.[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=O.[CH2:16]([NH2:19])[CH2:17][CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]1[NH:19][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8028TetrahydrofuranHCID 119832-IndanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17221237N-propyl-2,3-dihydro-1H-inden-2-amineYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A tetrahydrofuran (150 mL) solution of 2-indanone (11.0 g, 92 mmol), propyl amine (12 mL, 146 mmol), sodium triacetoxy borohydride (35.0 g, 165 mmol), and acetic acid (5 mL) was stirred at ambient temperature for 1 hour. The solution was then heated at reflux temperature for 2 hours. After cooling, the solvent was evaporated and the residue taken up in concentrated hydrochloric acid (40 mL). The acidic solution was washed with diethyl ether and then basified (10M sodium hydroxide). Extraction of the aqueous layer with ether, drying over anhydrous sodium carbonate and removal of the solvent yielded 10.9 g of the title compound as a yellow oil (75%).:

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. washThe acidic solution was washed with diethyl ether
  6. extractionExtraction of the aqueous layer with ether
  7. dry with materialdrying over anhydrous sodium carbonate and removal of the solvent

Sources & evidence

ORD record
ord-4e56bc2cf9c248f8997268761c4523de
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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