1-Isopropylpiperazine → 2-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014359Notes

Reaction equation

[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[CH:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([CH3:22])[CH3:21]>CO>[CH3:21][CH:20]([N:23]1[CH2:28][CH2:27][N:26]([CH2:3][CH2:2][C:1]([N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=3)[CH2:6]2)=[O:4])[CH2:25][CH2:24]1)[CH3:22]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (425 mg, 1.62 mmol) in methanol (5 mL) was treated with 1-isopropylpiperzine (1.0 mL, 7.0 mmol, Oakwood Products) and heated at 65° C. in a sealed tube for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was separated, dried over magnesium sulfate, filtered, and purified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane) to give 2-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (285 mg, 0.731 mmol, 45%). ESIMS (M+H)+=391.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
custompartitioned between ethyl acetate and saturated aqueous ammonium chloride
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
custompurified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane)

Sources & evidence

ORD record: ord-5d23273814da4404bac5057f7c93d49e
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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