Dimethylamine, hydrochloride → HCID 6502480, compound

HRID 1825746Notes

Reaction equation

HRID 1825746 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5]1.Cl.[CH3:17][NH:18][CH3:19].[OH-].[K+]>CO>[OH:1][CH:2]([CH2:15][N:18]([CH3:19])[CH3:17])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[CH:5]1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 14797Potassium HydroxideHCID 22139194HCID 22139194, compound

Product 1

HCID 6502480HCID 6502480, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2,3-epoxypropyl)indole-3-carboxaldehyde (0.5 g, 2.5 mmol), N,N-dimethylamine hydrochloride (4 g, 49 mmol) and anhydrous potassium hydroxide (2.75 g, 49 mmol) was stirred in dry methanol (50 ml) at −30° C. for 8 h., then allowed to slowly warm to room temperature. The mixture was concentrated under reduced pressure to half the original volume, then water was added and the mixture was extracted with dichloromethane. After drying with anhydrous sodium sulfate the solvent was removed under reduced pressure, and the oily residue was chromatographed on a silica gel column (eluent dichloromethane:methanol from (9:1) to (8:2)) to yield the entitled product as a yellow oil 0.49 g (80%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure to half the original volume
  2. additionwater was added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialAfter drying with anhydrous sodium sulfate the solvent
  5. customwas removed under reduced pressure
  6. customthe oily residue was chromatographed on a silica gel column (eluent dichloromethane:methanol from (9:1) to (8:2))

Sources & evidence

ORD record
ord-2c2394ef70884e98b00b798ac4862ba3
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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