Benzoyl chloride → HCID 13701395, compound

HRID 1906744Notes

Reaction equation

HRID 1906744 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.[OH-].[Na+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1.O>[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:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 136966832-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diol

Product 1

HCID 13701395HCID 13701395, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

0.01 mole (2.7 g) of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is dissolved in 50 ml of benzene with slight warming, and a solution of 0.015 mole (0.6 g) of sodium hydroxide in 10 ml of water is added to the solution. 0.011 mole (0.5 g) of benzoyl chloride is added dropwise to the reaction mixture, under cooling and stirring. When the addition of acid chloride is complete, the mixture is stirred at room temperature for one hour, whereupon the organic phase is separated, and the aqueous phase is extracted twice with chloroform. The combined organic phases are dried and evaporated to yield the aimed compound.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture is stirred at room temperature for one hour, whereupon the organic phase
  3. customis separated
  4. extractionthe aqueous phase is extracted twice with chloroform
  5. customThe combined organic phases are dried
  6. customevaporated

Sources & evidence

ORD record
ord-584e40e9ad1647159cc709a1cedba298
Source dataset
uspto-grants-1987_03
Patent number
US04654351

Reaction notes

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