Triethylamine → Nicainoprol

HRID 1156270Notes

Reaction equation

HRID 1156270 reaction equation
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[OH:19])[CH2:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O[C:21]1C=CC=[C:25]2[C:30]=1[NH:29][CH2:28][CH2:27][CH2:26]2.Cl.C(Cl)(=[O:39])C1C=CC=NC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[O:19][CH2:26][CH:27]([OH:39])[CH2:28][NH:29][CH:30]([CH3:25])[CH3:21])[CH2:12][CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2414901,2,3,4-Tetrahydroquinolin-8-olHCID 30187391,2,3,4-Tetrahydro-1-(3-pyridylcarbonyl)quinolin-8-ol

Product 1

HCID 71147Nicainoprol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

40 g of 1-nicotinoyl-8-hydroxy-1,2,3,4-tetrahydroquinoline ##STR9## are dissolved in 300 ml of dimethylformamide and 21 g of potassium tert.-butylate are then added at 5° C., while stirring. The mixture is stirred at 5° C. for 20 minutes, 66 g of epichlorohydrin are then added dropwise at this temperature, while stirring, and the mixture is then allowed to warm to room temperature and is subsequently stirred for 20 hours. Thereafter, the mixture is concentrated under a waterpump vacuum. The oil which remains is dissolved in water/toluene; the toluene phase is separated off, washed twice with dilute aqueous sodium hydroxide solution and once with water, dried and concentrated under a waterpump vacuum. A solid residue, which can be reacted directly with isopropylamine to give 1-nicotinoyl-8-[(3-isopropylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinoline, remains. The 1-nicotinoyl-8-hydroxy-1,2,3,4-tetrahydroquinoline used as the starting material is obtained in the customary manner by reacting 8-hydroxy-1,2,3,4-tetrahydroquinoline with nicotinic acid chloride hydrochloride in toluene at room temperature in the presence of triethylamine. (Melting point: 122° C.).

Workup

  1. customis obtained in the customary manner
  2. customat room temperature

Sources & evidence

ORD record
ord-da90f66a374a45e4bce9591ced0df101
Source dataset
uspto-grants-1982_06
Patent number
US04335123

Reaction notes

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