Sodium Iodide → HCID 19087645, compound

HRID 1464277Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:12]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl.[C:26]1([C:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:26]1([C:32]2[CH2:37][CH2:36][N:35]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:12]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:13]=3[C:14]([O:16][CH3:17])=[O:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:34][CH:33]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 2-[N-(4-chlorobutyl)-N-ethoxycarbonylamino]-4-nitrobenzoate (2.20 g), 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (1.32 g), sodium iodide (921 mg), and potassium carbonate (1.69 g) in dry dimethylformamide (30 ml) was stirred at 80° C. for 16 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate. Combined organic extract was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The crude residue was chromatographed on silica gel (40 g), eluting with a mixed solvent of chloroform and methanol (50:1 V/V) to give methyl 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl}-N-ethoxycarbonylamino]-4-nitrobenzoate (1.58 g).

Workup

extractionextracted with ethyl acetate
extractionCombined organic extract
washwas washed in turn with water and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe crude residue was chromatographed on silica gel (40 g)
washeluting with a mixed solvent of chloroform and methanol (50:1 V/V)

Sources & evidence

ORD record: ord-a26395caf9e647bc9430291beb8142b2
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304560

Reaction notes

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