Benzyl Bromide → HCID 20278981, compound

HRID 1248182Notes

Reaction equation

HRID 1248182 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N:9]=[CH:10][C:11]([CH:12]=1)=[C:6]23.[CH2:23]([Br:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[Mg]I>>[Br-:30].[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[C:5]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH:7]3[CH2:8][N+:9]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:10][C:11]([CH:12]=1)=[C:6]23

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 13472769HCID 13472769, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 20278981HCID 20278981, compound

Procedure

By following serially the procedure of step (a) of example 5 and the procedure of example 6 and selecting 5,6-dimethoxy-1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline as the starting material of formula II, benzyl bromide as the organohalide and methyl magnesium iodide as the Grignard reagent, (3,12b-trans)-5,6-dimethoxy-3-methyl-2-(phenylmethyl)-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline, mp 160°-162° C., NMR (CDCl3) δ6.5 (s, 1H), 7.25 (m, 9H), was obtained via 5,6-dimethoxy-2-phenylmethyl-1,7,8,12b-tetrahydrobenzo-[6,7]cyclohepta[1,2,3-de]isoquinolinium bromide, mp 196° C. (dec), NMR (DMSO-d6) δ 3.85 & 3.95 (2s, 6H), 5.15 (m, 1H), 5.32 & 5.62 (2d, J=13.7 Hz, 2H), 6.1-7.8 (m, 10H), 9.6 (s, 1H).

Sources & evidence

ORD record
ord-0b0ab4de944044bd950f109c708e5861
Source dataset
uspto-grants-1985_06
Patent number
US04522946

Reaction notes

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