N,N-Dimethylaminoethyl chloride hydrochloride → HCID 11280634, compound

HRID 855905Notes

Reaction equation

HRID 855905 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5]Cl.[F:8][C:9]1[CH:28]=[CH:27][C:12]2[S:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]3[S:17][C:18]([CH2:21][OH:22])=[N:19][C:20]=3[C:11]=2[CH:10]=1>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[F:8][C:9]1[CH:28]=[CH:27][C:12]2[S:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]3[S:17][C:18]([CH2:21][O:22][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])=[N:19][C:20]=3[C:11]=2[CH:10]=1

Participants

7

Reactant 2

HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 69369316HCID 69369316, compound

Product 1

HCID 11280634HCID 11280634, compound

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-dimethylaminoethylchloride-hydrochloride (12 mmoles) in 50% sodium hydroxide (5 ml), benzyltriethylammonium chloride (0.65 mmole) and a solution of the alcohol 80 (1.1 mmole) in toluene (5 ml) were added. The reaction mixture was heated under vigorous stirring and refluxing for 3 hours. Then it was cooled to room temperature, diluted with water and extracted with dichloromethane. After purification by chromatography on a silica gel column, an oily product was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 3 hours
  3. extractionextracted with dichloromethane
  4. customAfter purification by chromatography on a silica gel column
  5. customan oily product was isolated

Sources & evidence

ORD record
ord-8302dc74c22a4067b7a6a7f254d08fee
Source dataset
uspto-grants-2007_08
Patent number
US07262302B2

Reaction notes

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