Methyl iodide → HCID 13472773, compound

HRID 1248178Notes

Reaction equation

HRID 1248178 reaction equation
CI.C([I:5])C.[CH2:6]([N:8]1[CH2:17][CH:16]2[C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][CH2:21][C:14]3[C:15]2=[C:10]([C:11]([O:28][CH3:29])=[C:12]([O:26][CH3:27])[CH:13]=3)[CH2:9]1)[CH3:7]>>[I-:5].[CH2:6]([N+:8]1[CH2:17][CH:16]2[C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][CH2:21][C:14]3[C:15]2=[C:10]([C:11]([O:28][CH3:29])=[C:12]([O:26][CH3:27])[CH:13]=3)[CH:9]=1)[CH3:7]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6340IodoethaneHCID 13472782HCID 13472782, compound

Product 1

HCID 13472773HCID 13472773, compound

Procedure

By following the two step procedure of example 4, but replacing methyl iodide with an equivalent amount of ethyl iodide, 2-ethyl-4,5-dimethoxy-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline; mp 105°-106° C.; NMR (CDCl3) δ 1.29 (t, J=7 Hz, 3H), 2.65 (t,J=7 Hz, 2H), 3.69 & 3.73 (2s, 6H), 4.55 (t, J=4 Hz, 1H), 6.41 (s, 1H), 7.10 (m, 3H), 7.35 (m, 1H); Anal Calcd for C21H25NO2 : C, 77.98% H, 7.79% N, 4.33%; Found: C, 78.17% H, 8.21% N, 4.33%, was obtained via the quaternary Schiff base, 2-ethyl-4,5-dimethoxy-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinolinium iodide, mp 179°-181° C.; NMR (CDCl3) δ 1.78 (t, 3H), 3.84 & 3.92 (2s, 6H), 5.25 (m, 1H), 6.9-7.4 (m, 4H), 7.8 (s, 1H), 10.0 (s, 1H); IR (CHCl3) 1660 cm-1.

Sources & evidence

ORD record
ord-270f7e0c6c634c04aeaeb25b9165e319
Source dataset
uspto-grants-1985_06
Patent number
US04522946

Reaction notes

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