2-Bromopyridine → 2-Pyridinamine, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

HRID 1710079Notes

Reaction equation

HRID 1710079 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C(Cl)(Cl)Cl.CO>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 100192372-Pyridinamine, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (20 g) and 2-bromopyridine (12.64 g) were stirred at 125° C. for 31/2 days. The cooled reaction mixture was subjected to column chromatography on silica ((chloroform:methanol 10:1) to afford the title compound as an oil. This was treated with maleic acid in ethanol to give, on addition of diethyl ether, as a white solid 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]pyridine dimaleate (11.40 g), m.p. 116°-7° C. (recrystallised from isopropanol).

Workup

  1. customThe cooled reaction mixture

Sources & evidence

ORD record
ord-d059df1e19904fdd9effda8132d2bc5e
Source dataset
uspto-grants-1990_08
Patent number
US04952589

Reaction notes

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