2-Morpholinoethylamine → 2-Methyl-4-(n-2-morpholinoethyl)amino-8-(2,4,6-tri-methylphenyl)-quinoline

HRID 1700117Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][NH2:30])[CH2:24][CH2:23]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:11]=[C:10]([NH:30][CH2:29][CH2:28][N:25]2[CH2:26][CH2:27][O:22][CH2:23][CH2:24]2)[C:9]2[C:4](=[C:5]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Part C: To a solution of 5.1 g (17.1 mmol) of 2-methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline and 2.68 g (20.6 mmol) of 2-morpholinoethylamine in 150 ml of toluene, after bubbling through nitrogen gas for 30 minutes, a quantity of 2.29 g (23.9 mmol) sodium tertiary butoxide, 0.16 g (0.26 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (BINAP) and 0.082 g (0.09 mmol) Pd2(dibenzylideneacetone)3 were subsequently added. After heating to 100° C. for 16 hours and subsequent cooling, the reaction mixture was filtered and concentrated in vacuo. The product was purified on a silicagel column using CH2Cl2/MeOH/NH4OH 93:7:0.5 as the eluent. A total of 2.65 g of 2-methyl-4-(N-2-morpholinoethyl)amino-8-(2,4,6-tri-methylphenyl)-quinoline was obtained (40% yield).

Workup

filtrationsubsequent cooling, the reaction mixture was filtered
concentrationconcentrated in vacuo
customThe product was purified on a silicagel column

Sources & evidence

ORD record: ord-f21a96ba16364a04aa84069a588f00d1
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350750B1

Reaction notes

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