Potassium Hydroxide → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

HRID 2234229Notes

Reaction equation

[OH-].[K+].[CH3:3][N:4]([CH2:6][CH2:7][C@@H:8]([O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH3:5]>CS(C)=O>[CH3:3][N:4]([CH2:6][CH2:7][CH:8]([O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH3:5]

Participants

Conditions

Temperature: 100 °C

Procedure

Ground KOH (1.2 g) is added to a solution of (R)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine (3.1 g) in DMSO (10 ml), bubbled with a moderate stream of nitrogen, and the mixture is stirred and heated at 100° C. for 1 hour. After cooling down to lab temperature, the mixture is diluted with water (30 ml) and the racemic product is extracted with toluene. After evaporation, 2.6 g (84%) of (RS)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine is obtained.

Workup

custombubbled with a moderate stream of nitrogen
temperatureAfter cooling down to lab temperature
additionthe mixture is diluted with water (30 ml)
extractionthe racemic product is extracted with toluene
customAfter evaporation

Sources & evidence

ORD record: ord-9fb14caa92de4d6087d89890a2d8cfba
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709662B2

Reaction notes

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