Acetic Acid → HCID 14595362, compound

HRID 1731733Notes

Reaction equation

HRID 1731733 reaction equation
[OH:1][CH2:2][CH:3]([CH2:20][OH:21])[CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH2:18][CH3:19])=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=2)[CH2:7][CH2:6][NH:5]1.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C(O)(=O)C>C1C=CC=CC=1>[OH:1][CH2:2][CH:3]1[CH:4]2[C:13]3[C:8]([CH2:7][CH2:6][N:5]2[CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:21][CH2:20]1)=[CH:9][C:10]([O:17][CH2:18][CH3:19])=[C:11]([O:14][CH2:15][CH3:16])[CH:12]=3

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 136966852-(6,7-Diethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)propane-1,3-diol

Product 1

HCID 14595362HCID 14595362, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 mmoles (2.8 g) of 1-[bis(hydroxymethyl)-methyl]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline and 11 mmoles (1.17 g) of freshly distilled benzaldehyde are refluxed in 50 ml of absolute benzene, in the presence of a catalytic amount of hydrochloric acid or acetic acid for 4 hours. The solvent is distilled off and the residual pale-yellow oil is crystallized by trituration with ether. The aimed compound is obtained in a yield of 70%.

Workup

  1. distillationThe solvent is distilled off
  2. customthe residual pale-yellow oil is crystallized by trituration with ether

Sources & evidence

ORD record
ord-5079358a12114027ba98dfdbee244771
Source dataset
uspto-grants-1986_11
Patent number
US04623647

Reaction notes

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