Epichlorohydrin → 6-(2,3-Epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinoline

HRID 597208Notes

Reaction equation

HRID 597208 reaction equation
[OH-].[Na+].[CH:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH2:6]1)=[O:4].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>O>[O:20]1[CH2:19][CH:18]1[CH2:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][N:5]([CH:3]=[O:4])[CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 214470386-Hydroxy-3,4-dihydroisoquinoline-2(1H)-carbaldehyde

Product 1

HCID 214470066-(2,3-Epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydroisoquinolineYield 82.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.8 g of sodium hydroxide in 90 ml of water is added dropwise over 1 hour to a mixture of 26.6 g of 2-formyl-1,2,3,4-tetrahydro-6-hydroxy-isoquinoline and 42.5 g of epichlorohydrin at 60° C. The reaction mixture is held at this temperature for an additional hour, then allowed to cool and extracted several times with methylene chloride. The organic phase, dried over sodium sulfate, is evaporated and the residue is rubbed with diethyl ether. 29.0 g of 6-(2,3-epoxy-propoxy)-2-formyl-1,2,3,4-tetrahydro isoquinoline are obtained. m.p. = 78° - 79° C. (ethyl acetate - diethyl ether).

Workup

  1. waitThe reaction mixture is held at this temperature for an additional hour
  2. temperatureto cool
  3. extractionextracted several times with methylene chloride
  4. dry with materialThe organic phase, dried over sodium sulfate
  5. customis evaporated

Sources & evidence

ORD record
ord-3c13fef567cf42eabfbe987643084982
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

Loading…