Toluene → HCID 10287008, compound

HRID 2115265Notes

Reaction equation

HRID 2115265 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[O: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>[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][O:35][CH2:34][C:16]1[S:17][CH:18]=[C:19]2[C:25]=1[C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=1[O: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 10308260HCID 10308260, compound

Product 1

HCID 10287008HCID 10287008, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a 3-dimethylaminopropylchloride-hydrochloride solution (2.5 mmoles) in 50% sodium hydroxide (3 ml), benzyltriethylammonium chloride (0.3 mmole) and a toluene solution of the alcohol 12 (0.25 mmole) were added. The reaction mixture was heated under vigorous stirring and refluxing for 4 hours. Then it was cooled to room temperature, diluted with water and extracted with dichloromethane. After purification by column chromatography an oily product was isolated.

Workup

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

Sources & evidence

ORD record
ord-5edd44d41e5c4697986cf8980675a466
Source dataset
uspto-grants-2008_10
Patent number
US07435834B2

Reaction notes

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