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

HRID 542197Notes

Reaction equation

HRID 542197 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 70%

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, and the mixture is kept at 100 C.° for 10 hours. After cooling, 50 ml of a 15% aqueous hydrogen chloride solution is added to the reaction mixture, which is then evaporated under reduced pressure. The residue is thoroughly dehydrated and 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. temperatureAfter cooling
  2. customis then evaporated under reduced pressure
  3. customtriturated with a small amount of acetone

Sources & evidence

ORD record
ord-13d069e5802c434cb7a935ae8031ff0d
Source dataset
uspto-grants-1987_04
Patent number
US04656179

Reaction notes

Loading…