Diisopropylethylamine → 1-[(7-Methoxy-1,2,3,4-tetrahydro-naphth-2-yl)methyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester

HRID 2165160Notes

Reaction equation

HRID 2165160 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10]2)=[CH:5][CH:4]=1.Br.[CH3:26][O:27][C:28]([C:30]1[CH2:31][NH:32][CH2:33][CH2:34][CH:35]=1)=[O:29].C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:26][O:27][C:28]([C:30]1[CH2:31][N:32]([CH2:13][CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:33][CH2:34][CH:35]=1)=[O:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11210176p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) esterHCID 15560296Guvacoline Hydrobromide

Product 1

HCID 540184801-[(7-Methoxy-1,2,3,4-tetrahydro-naphth-2-yl)methyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.19 g (15 mmol) of p-toluene-sulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester in 75 ml of dimethylformamide there are added first 3.66 g (16.5 mmol) of 1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide (guvacoline hydrobromide) and then 6.78 g (52.5 mmol) of N-ethyl-N,N-diisopropylamine. The mixture is stirred at 60° for 18 hours and then concentrated by evaporation under a high vacuum. Water is added to the residue and extraction is carried out with diethyl ether. The organic phases are washed with water and extracted with 2N hydrochloric acid. The hydrochloric acid extracts are rendered alkaline at reduced temperature with sodium hydroxide solution (30%) and are extracted with dichloromethane, whereupon the combined organic phases are dried over sodium sulphate and concentrated by evaporation under reduced pressure. 1-[(7-methoxy-1,2,3,4-tetrahydro-naphth-2-yl)methyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester is obtained in the form of a light-yellow oil.

Workup

  1. concentrationconcentrated by evaporation under a high vacuum
  2. additionWater is added to the residue and extraction
  3. washThe organic phases are washed with water
  4. extractionextracted with 2N hydrochloric acid
  5. extractionare extracted with dichloromethane, whereupon the combined organic phases
  6. dry with materialare dried over sodium sulphate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b4020bf7a55a4a92ab21c6a983e7ce5e
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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