4-(4-Bromobenzyl)morpholine → 4-(Morpholinomethyl)aniline

HRID 472351Notes

Reaction equation

HRID 472351 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:34]=[CH:33][C:25]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:24][CH:23]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[CH:33][CH:34]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4].[N:27]1([CH2:26][C:25]2[CH:33]=[CH:34][C:22]([NH2:16])=[CH:23][CH:24]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 7835034-(4-Bromobenzyl)morpholineHCID 674790495-(4-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 2

HCID 7768514-(Morpholinomethyl)anilineYield 176.6%HCID 59612492[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine

Procedure

[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (125 mg, 0.43 mmol) and 4-(4-bromobenzyl)morpholine (122 mg, 0.48 mmol) in a manner analogous to Example 77 to yield 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine (73 mg, 37%) as an off-white powder following purification on a 4 g Isco silica gel column using methanol in dichloromethane (0-20%) as eluent. MP=222-223° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.66 (s, 1H), 8.32 (d, J=7.50 Hz, 2H), 8.15 (d, J=7.50 Hz, 2H), 7.66 (m, 4H), 7.30 (d, J=6.42 Hz, 1H), 7.20 (d, J=8.60 Hz, 2H), 3.55 (br s, 4H), 3.40-3.32 (m, 5H), 2.32 (br s, 4H). MS=465 (MH)+.

Sources & evidence

ORD record
ord-0ec6f846a1954bc481a0cd191eda99f6
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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