2-Iodobutane → HCID 59441905, compound

HRID 1014371Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.I[CH:17]([CH2:19][CH3:20])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][N:8]([CH:17]([CH3:18])[CH2:19][CH3:20])[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 65 °C

Procedure

6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (222 mg, 1.07 mmol) was dissolved in acetonitrile (5 mL), treated with 2-iodobutane (0.40 mL, 3.5 mmol) and potassium carbonate (500 mg, 3.62 mmol, Aldrich). The mixture was heated at 65° C. for 16 h, cooled, and partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, filtered, concentrated, and purified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia) to provide 6-(methyloxy)-2-(1-methylpropyl)-7-nitro-1,2,3,4-tetrahydro isoquinoline (0.23 g, 0.89 mmol, 82%). 1H NMR (400 MHz, CDCl3) δ ppm 0.96 (t, J=7.2 Hz, 3 H), 1.06-1.18 (m, 3 H), 1.37-1.48 (m, 1 H), 1.63 (m, signal overlapped with H2O, 1 H), 2.64-3.08 (m, 5 H), 3.63-3.85 (m, 2 H), 3.93 (s, 3 H), 6.81 (s, 1 H), 7.63 (s, 1 H); ESIMS (M+H)+=265.

Workup

temperaturecooled
custompartitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by chromatography on SiO2 (0 to 20% methanol/dichloromethane spiked with aqueous ammonia)

Sources & evidence

ORD record: ord-caf82a6427164beba8fb8fb1d09bcb5b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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