4-(2-Chloroethyl)morpholine → HCID 18422108, compound

HRID 1281716Notes

Reaction equation

HRID 1281716 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14])=[O:6].[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38]Cl)[CH2:33][CH2:32]1>>[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:1][C:2]2[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=2)[C:5]([NH:7][C:8]2[CH:9]=[C:10]([NH:15][C:16]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[CH:21]4)=[O:17])[CH:11]=[CH:12][C:13]=2[CH3:14])=[O:6])[CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 18422129HCID 18422129, compound

Product 1

HCID 18422108HCID 18422108, compoundYield 41%

Conditions

Temperature
40 °C

Procedure

Using an analogous procedure to that described in Example 7 except that the reaction mixture was heated to 70° C. rather than 40° C., N-[3-(3-hydroxybenzamido)-4-methylphenyl]quinoline-6-carboxamide was reacted with 2-morpholinoethyl chloride to give the title compound in 41% yield, m.p. 216-217° C.; NMR Spectrum: (DMSOd6) 2.21 (s, 3H), 2.47 (m, 4H), 2.73 (t, 2H), 3.59 (t, 4H), 4.18 (t, 4H), 7.17 (m, 1H), 7.24 (d, 1H), 7.42 (t, 1H), 7.54 (s, 2H), 7,61 (m, 2H), 7.87 (s, 1H), 8.15 (d, 1H), 8.23 (m, 1H), 8.52 (m, 1H), 8.61 (s, 1H), 9.0 (d, 1H), 9.9 (s, 1H), 10.49 (s, 1H); Mass Spectrum: M+H+ 511.

Sources & evidence

ORD record
ord-0faee0fac12f4d59a7197fe8ddea6c76
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

Loading…