Toluene → HCID 10150374, compound

HRID 2115268Notes

Reaction equation

HRID 2115268 reaction equation
Cl.Cl[CH2:3][CH2:4][CH2:5][NH2:6].C1(C)C=CC=CC=1.[Cl:14][C:15]1[CH:34]=[CH:33][C:18]2[O:19][C:20]3[CH:32]=[CH:31][CH:30]=[CH:29][C:21]=3[C:22]3[C:26]([C:17]=2[CH:16]=1)=[CH:25][S:24][C:23]=3[CH2:27][OH:28]>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:14][C:15]1[CH:34]=[CH:33][C:18]2[O:19][C:20]3[CH:32]=[CH:31][CH:30]=[CH:29][C:21]=3[C:22]3[C:26]([C:17]=2[CH:16]=1)=[CH:25][S:24][C:23]=3[CH2:27][O:28][CH2:3][CH2:4][CH2:5][NH2:6]

Participants

7

Reactant 3

HCID 1140TolueneHCID 10308545HCID 10308545, compoundHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 10150374HCID 10150374, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-chloropropylamine-hydrochloride (2.2 mmoles) in 50% sodium hydroxide (3 ml), benzyltriethylammonium chloride (0.3 mmole) and toluene solution of the alcohol 13 (0.22 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 with dichloromethane. After purification by column chromatography an oily product was isolated.

Workup

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

Sources & evidence

ORD record
ord-98e9f4c758f741cc8f8e1ed95a994a0b
Source dataset
uspto-grants-2008_10
Patent number
US07435834B2

Reaction notes

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