Diisopropylethylamine → HCID 57052772, compound

HRID 2165150Notes

Reaction equation

HRID 2165150 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[CH3:13][O:14][C:15]([C:17]1[CH2:22][NH:21][CH2:20][CH2:19][CH:18]=1)=[O:16].Br.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:13][O:14][C:15]([C:17]1[CH2:22][N:21]([CH2:2][CH2:3][CH:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:20][CH2:19][CH:18]=1)=[O:16]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1232286838434-35-4HCID 15560296Guvacoline Hydrobromide

Product 1

HCID 57052772HCID 57052772, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4.5 g (20 mmol) of 1-bromo-2-(indan-1-yl)-ethane are dissolved in 20 ml of toluene and added, at room temperature, to a solution of 4.9 g of guvacoline hydrobromide (20 mmol) and 5.7 g (44 mmol) of N,N-diisopropyl-N-ethylamine in 15 ml of dimethylformamide. The mixture is stirred at 45° under nitrogen for 12 hours. The solvents are then substantially removed under reduced pressure. The residue is rendered acidic with 2N hydrochloric acid and the aqueous solution is extracted with diethyl ether. The acidic aqueous phases are rendered basic with saturated sodium bicarbonate solution and extracted by shaking with diethyl ether. The organic phases are separated off, washed with saturated sodium chloride solution and dried over magnesium sulphate. 1-[2-(indan-1-yl)ethyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester is obtained.

Workup

  1. customThe solvents are then substantially removed under reduced pressure
  2. extractionthe aqueous solution is extracted with diethyl ether
  3. extractionextracted
  4. stirringby shaking with diethyl ether
  5. customThe organic phases are separated off
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-f87174129050429fb6d978c5a478593c
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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