18-Crown-6 → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

HRID 2234230

Reaction equation

HRID 2234230 reaction equation
C(O[K])(C)(C)C.C1OCCOCCOCCOCCOCCOC1.[CH3:25][N:26]([CH2:28][CH2:29][C@H:30]([O:36][C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[CH3:27]>S1(CCCC1)(=O)=O>[CH3:25][N:26]([CH2:28][CH2:29][CH:30]([O:36][C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)[CH3:27]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamineHCID 178418922HCID 178418922, compound

Product 1

HCID 11573192N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
110 °C

Procedure

tBuOK (16.8 g), and 18-crown-6 (0.25 g) are added to a solution of (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine (31 g) in sulfolane (100 ml), bubbled with a moderate stream of nitrogen, and the mixture is stirred and heated at 110° C. for 2 hours. After cooling down to lab temperature, the mixture is diluted with water (300 ml) and the racemic product is extracted with toluene. After evaporation, 25 g (81%) of RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine is obtained.

Workup

  1. custombubbled with a moderate stream of nitrogen
  2. temperatureAfter cooling down to lab temperature
  3. additionthe mixture is diluted with water (300 ml)
  4. extractionthe racemic product is extracted with toluene
  5. customAfter evaporation, 25 g (81%) of RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine
  6. customis obtained

Sources & evidence

ORD record
ord-779cc6060383413d999ea845235342a3
Source dataset
uspto-grants-2010_05
Patent number
US07709662B2

Linked notes

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