Sodium Carbonate → 6-{Propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol
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]2Participants
Procedure
13.1 kg (63.9 mol) (−)-5-hydroxy-N-n-propyl-2-aminotetralin, 51.6 kg (182 mol) 2-(2-thienyl)ethanol toluenesulfonate, and 4.1 kg (38.6 mol) sodium carbonate (0.6 molar ratio Na2CO3/amine starting material) were mixed in a reactor under a nitrogen atmosphere using xylenes (150 kg) as a solvent with vigorous agitation and heated to a temperature of 120° C. to 125° C. for a period of 32 hours. HPLC analysis of the reaction mixture showed less than 2% of the starting material remaining, and the reaction was halted. The product, (−)-5-hydroxy-2-[N-n-propyl-N-2-(2-thienyl)ethylamino]tetralin, was isolated in the usual manner well known to those skilled in the art without chromatographic purification to yield product that was converted to its hydrochloride salt form, with a yield of 13.2 kg (59%).
Workup
- temperatureheated to a temperature of 120° C. to 125° C. for a period of 32 hours
Sources & evidence
- ORD record
- ord-31169c7bd68b4425b2f218042dbbdf7b
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372920B1
Reaction notes
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