Hydrochloric Acid → 6,7-Dimethoxy-1-isochromanmethylamine

HRID 27771

Reaction equation

HRID 27771 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][OH:8].C(O[CH:17](OCC)[CH2:18][NH2:19])C.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:17]([CH2:18][NH2:19])[O:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 695242,2-DiethoxyethylamineHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 122258846,7-Dimethoxy-1-isochromanmethylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the starting material of formula II, 3,4-dimethoxyphenethyl alcohol (108 g), described by E. Z. Khafagy and J. P. Lambooy, J. Med. Chem. 9, 936 (1966), and the starting material of formula III, aminoacetaldehyde diethyl acetal (78 g), in dry dioxane (250 ml) is stirred and cooled (ice bath) while being saturated with hydrogen chloride over a period of one hour. The mixture is kept at room temperature for two days. The crystalline precipitate is collected, washed with dry dioxane and then ether to yield the hydrochloric acid addition salt (hydrochloride) of the title compound, m.p. 250°-255° C. (dec.), after recrystallization from methanol.

Workup

  1. temperaturecooled (ice bath)
  2. customThe crystalline precipitate is collected
  3. washwashed with dry dioxane
  4. customether to yield

Sources & evidence

ORD record
ord-1e2f3cdde0d746b2b8d98ffbdef4111e
Source dataset
uspto-grants-1980_09
Patent number
US04223151

Linked notes

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