Benzoyl chloride → HCID 13701395, compound

HRID 979487Notes

Reaction equation

HRID 979487 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 under slight warming, and the solution obtained is admixed with a solution of 0.015 mole (0.6 g) of sodium hydroxide in 10 ml of water. 0.011 mole (1.5 g) of benzoyl chloride is added dropwise to the reaction mixture under cooling and stirring. When the addition is complete, the reaction mixture is stirred at room temperature for an additional hour, the organic phase is separated, and the aqueous phase is extracted twice with chloroform. The organic phases are combined, dried and evaporated to yield the aimed compound with a melting point of 161° to 163° C. (methanol/ether).

Workup

  1. customthe solution obtained
  2. temperatureunder cooling
  3. additionWhen the addition
  4. stirringthe reaction mixture is stirred at room temperature for an additional hour
  5. customthe organic phase is separated
  6. extractionthe aqueous phase is extracted twice with chloroform
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-786b528ebd7e487989d880fb31013c17
Source dataset
uspto-grants-1987_05
Patent number
US04668688

Reaction notes

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