Tetrahydrofuran → HCID 58842532, compound

HRID 1270446Notes

Reaction equation

[CH2:1]1[C@@H:3]([NH2:4])[C@@H:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.Br[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1.O1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[N+:27]([C:26]1[C:21]([NH:4][CH2:3][C:2]2([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1][CH2:34][CH2:33][CH2:32][CH2:31]2)=[N:22][CH:23]=[CH:24][CH:25]=1)([O-:29])=[O:28]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 19493(1R,2S)-Tranylcypromine

HCID 81531Diisopropylethylamine

HCID 5550542-Bromo-3-nitropyridine

Product 1

HCID 58842532HCID 58842532, compound

Conditions

Temperature: 60 °C

Procedure

A solution of compound 1 (1.21 g; 6.39 mmol) in anhydrous tetrahydrofuran (30 mL) was treated with N,N-diisopropylethylamine (1 mL; 5.73 mmol) and 2-bromo-3-nitro-pyridine (1.18 g; 5.81 mmol). The reaction mixture was heated at 60° C. for 21 h. The solvent was removed under reduced pressure and the residue was treated with ethyl acetate and 10% aqueous hydrochloric acid. The organic layer was separated, washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered and concentrated. The product was purified by recrystallization from a minimum amount of ethyl acetate to provide 1.3 g of (3-nitro-pyridin-2-yl)-(1-phenyl-cyclohexylmethyl)-amine as light tan solid. Mass Spec [M+H]+=312.

Workup

customThe solvent was removed under reduced pressure
additionthe residue was treated with ethyl acetate and 10% aqueous hydrochloric acid
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried (anhydrous sodium sulfate)
filtrationfiltered
concentrationconcentrated
customThe product was purified by recrystallization from a minimum amount of ethyl acetate

Sources & evidence

ORD record: ord-502fb2089409414ebc84cef843560e12
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202253B2

Reaction notes

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