1-Fluoronaphthalene → N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

HRID 222782

Reaction equation

HRID 222782 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([OH:12])[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[OH-].[K+].F[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.[C:26]([OH:35])(=[O:34])[C@H:27]([C@@H:29]([C:31]([OH:33])=[O:32])[OH:30])[OH:28]>CS(C)=O.O>[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([O:12][C:24]1[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][CH:23]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:31]([C@H:29]([C@@H:27]([C:26]([O-:35])=[O:34])[OH:28])[OH:30])([O-:33])=[O:32]

Participants

7

Reactant 4

HCID 94501-FluoronaphthaleneHCID 14797Potassium HydroxideHCID 439655D-Tartaric acidHCID 115864093-(Dimethylamino)-1-(2-thienyl)-1-propanol

Product 1

HCID 86625060N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine (185 g, 1 mole), potassium hydroxide (112 g, 2 moles) and 1-fluoronaphthalene (146 g, 1 mole) in dimethylsulfoxide (1000 ml) is stirred at 110° C. for 2 hours. After cooling down to 20° C., the mixture is filtered, diluted with water (3 l), D-tartaric acid (75 g, 0.5 mole) is added and the mixture is stirred at 80° C. for 0.5 hour. After cooling down, the precipitated product is sucked off, washed with water and dried. Yield: 313 g (81%).

Workup

  1. temperatureAfter cooling down to 20° C.
  2. filtrationthe mixture is filtered
  3. additionis added
  4. stirringthe mixture is stirred at 80° C. for 0.5 hour
  5. temperatureAfter cooling down
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1f1d09bc99434a4088561b4461739bef
Source dataset
uspto-grants-2012_06
Patent number
US08207356B2

Linked notes

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