Sodium Carbonate → 6-{Propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 842314Notes

Reaction equation

HRID 842314 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([NH:12][CH2:13][CH2:14][CH3:15])[CH2:7]2.C1(C)C(S(O[CH2:26][CH2:27][C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([N:12]([CH2:13][CH2:14][CH3:15])[CH2:26][CH2:27][C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)[CH2:7]2

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 103756766-(propylamino)-5,6,7,8-tetrahydronaphthalen-1-olHCID 22619260HCID 22619260, compound

Product 1

HCID 575376-{Propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol

Procedure

700 mg (3.4 mmol) (−)-5-hydroxy-N-n-propyl-2-aminotetralin made by the process described in U.S. Pat. No. 5,382,596, 4.8 g (17 mmol) 2-(2-thienyl)ethanol toluenesulfonate, 216 mg (2 mmol) sodium carbonate (0.6 molar ratio Na2CO3/amine starting material), and 40 mL xylenes (mixture, Aldrich Chemical Co.) were mixed and brought to reflux. The reaction was halted at 24 hours, and worked up in the usual manner well known to those skilled in the art without chromatographic purification to yield the product, (−)-5-hydroxy-2-[N-n-propyl-N-2-(2-thienyl)ethylamino]tetralin, that was converted to its hydrochloride salt form, with a yield of 1 g (84%).

Workup

  1. temperatureto reflux
  2. customwithout chromatographic purification

Sources & evidence

ORD record
ord-8615915a7bb0444aafbbd319378ed231
Source dataset
uspto-grants-2002_04
Patent number
US06372920B1

Reaction notes

Loading…