Triethylamine → 1-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione

HRID 364615Notes

Reaction equation

HRID 364615 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.C(N(CC)CC)C.[C:27](Cl)(Cl)=[S:28]>C(Cl)(Cl)Cl>[OH:1][CH2:2][CH:3]1[CH:4]2[C:13]3[C:8]([CH2:7][CH2:6][N:5]2[C:27](=[S:28])[O:19][CH2:18]1)=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 136966832-(6,7-Dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-propane-1,3-diol

Product 1

HCID 148340121-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thioneYield 19%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.67 g (0.01 mole) of 1-[bis(hydroxymethyl)-methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline in 150 ml of absolute chloroform a solution of 2.0 g (0.02 mole) of triethyl amine in 10 ml of absolute chloroform is added, and to the mixture 1.15 g (0.01 mole) of thiophosgene are added dropwise with stirring, under cooling with ice. The reaction mixture is stirred for 10 minutes, then it is washed to neutral with 15 ml of a 5% hydrochloric acid solution and subsequently water. The chloroformic phase is dried over sodium sulfate and evaporated to dryness. The residue is taken up in 15 to 20 ml of ethanol, and ether is added to the mixture until slight turbidity. The desired compound is obtained in crystalline form.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe reaction mixture is stirred for 10 minutes
  3. washit is washed to neutral with 15 ml of a 5% hydrochloric acid solution and subsequently water
  4. dry with materialThe chloroformic phase is dried over sodium sulfate
  5. customevaporated to dryness
  6. additionether is added to the mixture until slight turbidity

Sources & evidence

ORD record
ord-622bb88ec64c4472acaee34e6f6c9a7f
Source dataset
uspto-grants-1986_08
Patent number
US04605653

Reaction notes

Loading…