Acetic Acid → 6-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 6751Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH:19]([NH2:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:24](O)(=O)C>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[CH2:24][NH:21][CH:19]([CH3:20])[CH2:18][C:12]2=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(5-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamine (58 mg, 0.21 mmol), 37% formaldehyde (17 uL, 0.23 mmol) and ethanol (2 ml) was heated in a sealed tube at 80° C. for 2 h. The mixture was cooled to rt and acetic acid (60.6 uL, 1.05 mmol) was added. The mixture was heated again in a sealed tube at 80° C. for 5 h. Evaporation of volatiles yielded 6-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline (40 mg).

Workup

temperatureThe mixture was cooled to rt
temperatureThe mixture was heated again in a sealed tube at 80° C. for 5 h
customEvaporation of volatiles

Sources & evidence

ORD record: ord-d05eca1dd2af4e6f9d22796c7e4a4373
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084154B2

Reaction notes

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