Triethylamine → 5-Nicotinoyl-Hexahydro-1H-Furo(3,4-c)Pyrrole

HRID 1283610Notes

Reaction equation

Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH2:11]1[CH:15]2[CH2:16][NH:17][CH2:18][CH:14]2[CH2:13][O:12]1.C(N(CC)CC)C>C1C=CC=CC=1>[C:2]([N:17]1[CH2:18][CH:14]2[CH2:13][O:12][CH2:11][CH:15]2[CH2:16]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

Conditions

Temperature: 15 °C

Procedure

Nicotinoyl chloride hydrochloride, represented by formula (XII), (0.1 mole, 17.81 grams) was slowly added to a mixture of hexahydro-1H-furo(3,4-c)pyrrole, represented by formula (X), (0.1 mole, 11.3 grams), and triethylamine (0.2 mole, 20.24 grams) in 160 ml of benzene at 15°C. The reaction mixture was stirred for 1.5 hours at 15°C. and then left overnight at room temperature. The HCl salt of triethylamine was filtered and the salt was washed with benzene. The washings were combined with the filtrate and benzene was stripped under vacuum. The product, 5-nicotinoyl-hexahydro-1H-furo(3,4-c)pyrrole, represented by formula (XIII), light yellow viscous liquid, was purified by column chromatography (Alumina-eluted with methyl acetate).

Workup

waitleft overnight at room temperature
filtrationThe HCl salt of triethylamine was filtered
washthe salt was washed with benzene
customwas purified by column chromatography (Alumina-eluted with methyl acetate)

Sources & evidence

ORD record: ord-76a60cd4b50b4fe28efe8c5fa51591bc
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03975532

Reaction notes

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