Boron trifluoride → 3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

HRID 979363Notes

Reaction equation

HRID 979363 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].B(F)(F)F.[N+](C1C=CC=CC=1)([O-])=O.[Cl-].Cl[CH2:20][CH:21]([NH+:41]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([O:52][CH3:53])[CH:45]=1)[CH3:42])[CH2:22][CH2:23][CH2:24][C:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=1)([C:29]#[N:30])[CH:26]([CH3:28])[CH3:27]>C(Cl)Cl.[N+](C)([O-])=O>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:25]([CH:26]([CH3:27])[CH3:28])([C:29]#[N:30])[CH2:24][CH2:23][CH2:22][CH:21]2[CH2:20][C:49]3[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=3)[CH2:43][N:41]2[CH3:42])[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 7416NitrobenzeneHCID 6451240Aluminum(III) Chloride2×HCID 20202193N-[1-chloro-6-(3,4-dimethoxyphenyl)-6-cyano-6-(prop-2-yl)hex-2-yl]-N-(3,4-dimethoxybenzyl)-N-methylammonium chloride

Product 1

HCID 1291023-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolvent

Procedure

The ammonium compound of formula 29 is then cyclized to form a compound of formula 1 (step 7). This reaction is performed using 1-1.5 moles of a Lewis acid, such as AlCl3, FeCl3, BF3, and the like, in a suitable aprotic solvent, preferably a halogenated hydrocarbon solvent, nitromethane, or nitrobenzene, particularly CH2Cl2, at a temperature of about -10° to about 80° C., for a period of about 10 minutes to about five hours, preferably about two hours. For example, N-[1-chloro-6-(3,4-dimethoxyphenyl)-6-cyano-6-(prop-2-yl)hex-2-yl]-N-(3,4-dimethoxybenzyl)-N-methylammonium chloride (29) is suspended in CH2Cl2 at 0° C. and stirred with 1.5 moles of AlCl3 for 2 hours to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1).

Workup

  1. custompreferably about two hours

Sources & evidence

ORD record
ord-67efc1fce5f746af88da07a2530c9eee
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

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