Toluene → HCID 9800087, compound

HRID 2115272Notes

Reaction equation

HRID 2115272 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6]Cl.C1(C)C=CC=CC=1.[C:16]1([CH2:34][OH:35])[S:17][CH:18]=[C:19]2[C:25]=1[C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[S:22][C:21]1[CH:30]=[CH:31][CH:32]=[CH:33][C:20]2=1>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:16]1([CH2:34][O:35][CH2:6][CH2:5][CH2:4][N:3]([CH3:8])[CH3:2])[S:17][CH:18]=[C:19]2[C:25]=1[C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[S:22][C:21]1[CH:30]=[CH:31][CH:32]=[CH:33][C:20]2=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 10149515HCID 10149515, compound

Product 1

HCID 9800087HCID 9800087, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-dimethylaminopropylchloride-hydrochloride (6.7 mmoles) in 50% sodium hydroxide (5 ml), benzyltriethylammonium chloride (0.88 mmole) and toluene solution of the alcohol 15 (0.67 mmole) were added. The reaction mixture was heated under vigorous stirring and refluxing for 5 hours. Then it was cooled to room temperature, diluted with water and extracted by dichloromethane. After purification by column chromatograpy an oily product was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 5 hours
  3. extractionextracted by dichloromethane
  4. customAfter purification by column chromatograpy an oily product
  5. customwas isolated

Sources & evidence

ORD record
ord-010913b120014d52a2ec19636b87fa1d
Source dataset
uspto-grants-2008_10
Patent number
US07435834B2

Reaction notes

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