Borane;tetrahydrofuran → 3,4-Methylenedioxybenzyl-(3-azepin-1-yl-propyl)-amine

HRID 1264529Notes

Reaction equation

HRID 1264529 reaction equation
[CH2:1]1[O:22][C:21]2[CH:20]=[CH:19][C:5]([CH2:6][N-:7][C:8](=O)[CH2:9][CH2:10][N:11]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][C:3]=2[O:2]1.B.C1COCC1>C1COCC1>[CH2:1]1[O:22][C:21]2[CH:20]=[CH:19][C:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuran2×HCID 178520819HCID 178520819, compound

Product 1

HCID 186126483,4-Methylenedioxybenzyl-(3-azepin-1-yl-propyl)-amineYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-methylenedioxybenzyl-(3-azepin-1-yl-propionyl)-amide (20 g, 69 mmole) was dissolved in THF and treated with a solution of Borane/THF (1M, 138 mL, 138 mmole) and heated to reflux for 5 hours. Added another 60 mL borane/THF and heated for 4 hours. The reaction was cooled to room temperature and quenched by the careful addition of ethanol (20 mL) and then 6 N HCl (100 mL). The mixture was concentrated at reduced pressure and redissolved in 6N HCl (200 mL) and methanol (100 mL) and heated gently for 15 minutes. After cooling the solution was extracted once with ether (100 mL) and then basified to pH 12 with aqueous sodium hydroxide. This was then extracted with ethyl acetate (3×200 mL) and the combined ethyl acetate extracts were dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure to give 15 g of the product. 1H NMR (CDCl3, 300 MHz) δ6.82 (s, 1H); 6.76 (s, 2H); 5.95 (s, 2H); 3.7 (s, 2H); 2.7-2.46 (m, 8H); 1.7-1.5 (m, 10H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureheated for 4 hours
  4. customquenched by the careful addition of ethanol (20 mL)
  5. concentrationThe mixture was concentrated at reduced pressure
  6. dissolutionredissolved in 6N HCl (200 mL)
  7. temperaturemethanol (100 mL) and heated gently for 15 minutes
  8. temperatureAfter cooling the solution
  9. extractionwas extracted once with ether (100 mL)
  10. extractionThis was then extracted with ethyl acetate (3×200 mL)
  11. dry with materialthe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-e55171181d624d0eb5fe8bebee55eeb4
Source dataset
uspto-grants-2003_04
Patent number
US06544982B1

Reaction notes

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