1-(But-3-yn-1-yl)piperidine → 4-[5-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-3-ylmethyl]-morpholine

HRID 30472Notes

Reaction equation

HRID 30472 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[N:6][CH:7]=1.[CH2:15]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][C:17]#[CH:18]>>[N:19]1([CH2:15][CH2:16][C:17]#[C:18][C:2]2[CH:3]=[C:4]([CH2:8][N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[CH:5]=[N:6][CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 131559861-(But-3-yn-1-yl)piperidineHCID 223904154-((5-Bromopyridin-3-yl)methyl)morpholine

Product 1

HCID 116093414-[5-(4-Piperidin-1-yl-but-1-ynyl)-pyridin-3-ylmethyl]-morpholine

Procedure

This compound was made in a similar way as described in Example 18, Step D, using 4-(5-bromo-pyridin-3-ylmethyl)-morpholine and 1-but-3-ynyl-piperidine (57%). MS (ESI): exact mass calcd. for C19H27N3O, 313.45; m/z found, 314.5 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.49 (d, J=1.9,1H), 8.40 (d, J=1.6,1H), 7.66-7.64 (m, 1H), 3.68 (t, J=4.5, 4H), 3.45 (s, 2H), 2.67-2.58 (m, 4H), 2.49-2.38 (m, 8H), 1.62-1.52 (m, 4H), 1.46-1.40 (m, 2H).

Sources & evidence

ORD record
ord-25c488fc0aa04321abbd095fd4f6b735
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

Loading…