1,2,3,4-Tetrahydroisoquinoline → HCID 9908293, compound

HRID 365488Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1[N:8]([CH2:9][CH3:10])[N:7]=[C:6]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])[C:5]=1[CH2:20][CH3:21].[CH2:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][NH:23]1.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C.O>[CH2:9]([N:8]1[C:4]([CH2:3][N:23]2[CH2:24][CH2:25][C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22]2)=[C:5]([CH2:20][CH3:21])[C:6]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[N:7]1)[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the product of step D (from above) and 1,2,3,4-tetrahydroisoquinoline (150 mg, 1.1 mmol) and triethylamine (1 mL in 5 mL of DMF was heated at 100° C. for 1 hour. The mixture was cooled, diluted with water, basified with 1 N NaOH, and finally extracted with ether. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give about 500 mg of the crude compound as an oil. The oil was purified through silica gel column chromatography to give 160 mg of the title compound as an oil. 1H NMR (CDCl3): 0.90 (t, 3H), 1.39 (t, 3H), 2.05 (s, 6H), 2.25 (q, 2H), 2.31 (s, 3H), 2.76 (q, 2H), 2.90 (q, 2H), 3.66 (s, 2H), 3.68 (s, 2H), 4.24 (q, 2H), 6.90 (s, 2H), 7.05 (m, 1H), 7.15 (m, 3H)ppm.

Workup

temperatureThe mixture was cooled
extractionfinally extracted with ether
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customto give about 500 mg of the crude compound as an oil
customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-5fb79d166a6843e99533809ef94d8129
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127399

Reaction notes

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