Triethylamine → N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexan-carboxamide

HRID 647590Notes

Reaction equation

[CH3:1][C:2]1([CH2:15][NH2:16])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.C(N(CC)CC)C.[CH:24]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>O1CCCC1>[CH3:1][C:2]1([CH2:15][NH:16][C:30]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:31])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine(2.6 g, described in Example 3), triethylamine (1.34 g), cyclohexylcarbonyl chloride (1.94 g) and dry tetrahydrofuran (60 ml) is stirred at 25° C. for 18 hours, filtered and evaporated. The residue is crystallized from benzene-hexane to obtain the title compound (3.8 g); mp 174°-175° C.; nmr (CDCl3) δ0.85-2.25(m), 1.55(s), 2.81(m), 3.79(m), 4.00(m), 5.96(t), 6.9-7.2(m) and 9.71(s).

Workup

filtrationfiltered
customevaporated
customThe residue is crystallized from benzene-hexane

Sources & evidence

ORD record: ord-de2b6ca2c1be44f1a00577935ef4194e
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04409224

Reaction notes

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