Benzene → 1-[bis(hydroxymethyl)-methyl]-2-[N'-phenylcarbamoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 979488Notes

Reaction equation

HRID 979488 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.C1C=CC=CC=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[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[C:33](=[O:34])[NH:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 7672Phenyl isocyanateHCID 136966832-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diol

Product 1

HCID 202005391-[bis(hydroxymethyl)-methyl]-2-[N'-phenylcarbamoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 91%

Procedure

To a solution of 0.01 mole (2.7 g) of 1-[bis-(hydroxymethyl)-methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline in 30 ml of absolute benzene 0.01 mole (0.3 g) of phenyl isocyanate is added, and the mixture is refluxed for 30 to 60 minutes. The reaction mixture is allowed to cool to room temperature, the precipitated crystals are filtered off, washed with ether and crystallized. The aimed compound is obtained with a melting point of 191° to 192° C. (ethyl acetate).

Workup

  1. temperaturethe mixture is refluxed for 30 to 60 minutes
  2. filtrationthe precipitated crystals are filtered off
  3. washwashed with ether
  4. customcrystallized

Sources & evidence

ORD record
ord-502fc6a25d0d4bceb706621ce97de6b2
Source dataset
uspto-grants-1987_05
Patent number
US04668688

Reaction notes

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