Hydrochloric Acid → 1-[Bis(hydroxymethyl)-methyl]-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 979486Notes

Reaction equation

HRID 979486 reaction equation
[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][NH:5]1.[CH2:20]=O.[ClH:22]>C(O)=O>[ClH:22].[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][N:5]1[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 136966832-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diol

Product 1

HCID 146445101-[Bis(hydroxymethyl)-methyl]-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 50%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 0.0125 mole (3.33 g) of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 15 ml of a 37% aqueous formaldehyde solution and 15 ml of 99% formic acid are added. The reaction mixture is then kept at 100° C. for 10 hours. After cooling 50 ml of a 15% aqueous hydrochloric acid solution are added to the reaction mixture, which is then evaporated under reduced pressure. After thoroughly dehydrating the reaction mixture it is triturated with a small amount of acetone to yield the aimed compound with a melting point of 199° to 201° C. (ethanol/ether).

Workup

  1. additionare added to the reaction mixture, which
  2. customis then evaporated under reduced pressure
  3. customis triturated with a small amount of acetone

Sources & evidence

ORD record
ord-d2fb38ba9e6641ad89a9b7456b6cf60d
Source dataset
uspto-grants-1987_05
Patent number
US04668688

Reaction notes

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