Methyl iodide → 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodide

HRID 979374Notes

Reaction equation

HRID 979374 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH:31]([CH3:33])[CH3:32])([C:29]#[N:30])[CH2:12][CH2:13][CH2:14][CH:15]2[CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:27][CH3:28])=[C:21]([O:25][CH3:26])[CH:22]=3)[CH:17]=[N:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:34][I:35]>CC(C)=O>[I-:35].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH:31]([CH3:33])[CH3:32])([C:29]#[N:30])[CH2:12][CH2:13][CH2:14][CH:15]2[CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:27][CH3:28])=[C:21]([O:25][CH3:26])[CH:22]=3)[CH:17]=[N+:16]2[CH3:34])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 202021823-[4-(3,4-Dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

Product 1

HCID 202022113-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The dihydroisoquinoline derivative of formula 40 is then N-alkylated using a compound of formula R3 -L to produce a 3,4-dihydroisoquinolinium derivative of formula 41 (step 2). For example, 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-3,4-dihydroisoquinoline (40) is dissolved in acetone with methyl iodide and heated at reflux to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodide (41).

Workup

  1. temperatureheated
  2. temperatureat reflux

Sources & evidence

ORD record
ord-f3a40d44b9b749baadba927633af2ef0
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

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