Dimethyl Sulfate → HCID 70357559, compound

HRID 1905456Notes

Reaction equation

HRID 1905456 reaction equation
COS([O:6][CH3:7])(=O)=O.[C-]#N.[Na+].C(C1C=CC=CN=1)#N.[NH:19]1[C:29]2[C:23](C=[CH:25][CH:26]=[C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]3=2)=[CH:22][CH:21]=[CH:20]1>>[O:6]=[C:7]1[C:23]2[CH:22]=[CH:21][CH:20]=[N:19][C:29]=2[C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[CH:26]=[CH:25]1

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 7522Pyridine-2-carbonitrileHCID 8929Sodium CyanideHCID 86743192HCID 86743192, compound

Product 1

HCID 70357559HCID 70357559, compound

Procedure

In a process described in U.S. Pat. No. 3,326,924, 3-(2-phenethyl)-2-cyanopyridine is prepared by reacting 3-(2-phenethyl)pyridine-1-oxide with dimethylsulfate and then with aqueous sodium cyanide. A process to convert the cyanopyridine to an aza-dibenzocycloheptene by cyclizing to give the 5-keto-aza-dibenzocycloheptene, then reacting with a Grignard reagent, e.g., 1-methyl-4-piperidinyl magnesium chloride, to give a 5-(1-methyl-4-piperidinyl)aza-dibenzocycloheptene-5-ol, which is dehydrated to give the exocyclic 5-(1-methyl-piperidylidenyl) compound, e.g., azatadine, is also described in U.S. Pat. No. 3,326,924.

Sources & evidence

ORD record
ord-ab90a232b8064419aaa4c70bb2dfcc29
Source dataset
uspto-grants-1989_06
Patent number
US04843163

Reaction notes

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