Formaldehyde → HCID 12264703, compound

HRID 1368193Notes

Reaction equation

HRID 1368193 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:16]=O>C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[CH2:16][NH:13][CH2:12][C:11]2([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 122597152-(3,4-dimethoxyphenyl)-2-methylpropan-1-amine

Product 1

HCID 12264703HCID 12264703, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A conventional alkylation reaction was carried out using a dimethylformamide solution (10 ml) of 1.77 g of 2-(3,4-dimethoxyphenyl)acetonitrile, 1.00 g of sodium hydride and 4.26 g of methyl iodide to give 1.78 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile. A conventional catalytic hydrogenation reaction was carried out using an ethanolic solution (30 ml) of 1.75 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile, 3.0 ml of an aqueous 28% ammonia solution and 4.3 g of Raney nickel to give 1.59 g of 2-(3,4-dimethoxyphenyl)-2-methylpropylamine. Then, a conventional cyclization reaction was carried out using a formic acid solution (8 ml) of 1.58 g of 2-(3,4-dimethoxyphenyl)-2-methylpropylamine and 0.252 g of paraformaldehyde to give 1.34 g of 6,7-dimethoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline as a pale yellow oily substance. A conventional alkylation reaction was carried out using a solution (10 ml) of 1.77 g of 2-(3,4-dimethoxyphenyl)acetonitrile in dimethylformamide, 1.00 g of sodium hydride and 4.26 g of methyl iodide to give 1.78 g of 2-(3,4-dimethoxyphenyl)-2-methylpropionitrile.

Workup

  1. customThen, a conventional cyclization reaction

Sources & evidence

ORD record
ord-2ba853626e614e9fbadbfaeaa85a6fca
Source dataset
uspto-grants-2003_06
Patent number
US06573279B1

Reaction notes

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