Sodium Hydroxide → HCID 66886979, compound

All of the 1,4,7-tri(n-heptylcarbonyl)-1,4,7-triazacyclononane was put into a 200 mL three neck flask provided with a reflux tube in an argon atmosphere, and a BH3.THF solution (100 mmol, 100 mL) was added thereto and reflowed for one night. To break down the excess BH3.THF, methanol was added slowly to the reaction mixture after allowing it to cool to room temperature, and after concentration, this was dissolved in 1-butanol (50 mL), water (50 mL) and concentrated hydrochloric acid (100 mL and reflowed for one night. The reaction mixture obtained was cooled in an ice bath, and a 48% aqueous solution of sodium hydroxide was added until the pH exceeded 12. After amine separation, this aqueous solution was extracted in methylene chloride (8×50 mL). After the organic layer that was obtained was dried using anhydrous sodium sulfate, it was concentrated, and pale yellow, oily 1,4,7-tri-n-octyl-1,4,7-triazacyclononane (2.45 g, 85% yield) was obtained.

1. customprovided with a reflux tube in an argon atmosphere
2. waitreflowed for one night
3. additionwas added slowly to the reaction mixture
4. concentrationafter concentration
5. dissolutionthis was dissolved in 1-butanol (50 mL)
6. waitwater (50 mL) and concentrated hydrochloric acid (100 mL and reflowed for one night
7. customThe reaction mixture obtained
8. temperaturewas cooled in an ice bath
9. customAfter amine separation
10. extractionthis aqueous solution was extracted in methylene chloride (8×50 mL)
11. customAfter the organic layer that was obtained
12. customwas dried
13. concentrationwas concentrated

ORD record

ord-855e472a57cb4a75be3e0f6ecd554753

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017706B2