Formaldehyde → HCID 69949954, compound

HRID 1420085Notes

Reaction equation

HRID 1420085 reaction equation
[CH2:1]=O.[NH:3]1[CH2:9][CH2:8][CH2:7][C@H:4]1[CH2:5][OH:6].[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.[OH-].[Na+]>C(O)(=O)C>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:1][N:3]2[CH2:9][CH2:8][CH2:7][C@H:4]2[CH2:5][OH:6])=[CH:12]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 117811-MethylindoleHCID 14798Sodium HydroxideHCID 640091L-Prolinol

Product 1

HCID 69949954HCID 69949954, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of formalin (0.33 ml, 48% in H2O) and acetic acid (0.9 ml) was added L-prolinol (0.43 g) with stirring under ice-cooling. After 5 min, 1-methyl indole (0.56 g) was added dropwise to the above reaction mixture, and stirring was continued for 2 h. At the end of this time, reaction mixture was basified with 2N NaOH; the oily residue was extracted with ethyl acetate, dried (Na2SO4), and the solvent was evaporated to dryness to give the title compound (0.87 g, 83%), as a white solid, mp. 46°-48° C.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. waitwas continued for 2 h
  4. customAt the end of this time, reaction mixture
  5. extractionthe oily residue was extracted with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-5361bdef948844899ae6b1e968703c48
Source dataset
uspto-grants-1999_03
Patent number
US05889032

Reaction notes

Loading…