Acetaldehyde → (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-ethyl-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amine

HRID 1019928Notes

Reaction equation

HRID 1019928 reaction equation
[CH:1](=O)[CH3:2].[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][NH:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24][C:25]4[CH:34]=[N:33][C:32]5[C:27](=[CH:28][C:29]([O:35][CH3:36])=[CH:30][CH:31]=5)[N:26]=4)[CH2:18][CH2:17]3)=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1>>[O:4]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][N:15]([CH2:1][CH3:2])[CH:16]3[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][S:24][C:25]4[CH:34]=[N:33][C:32]5[C:27](=[CH:28][C:29]([O:35][CH3:36])=[CH:30][CH:31]=5)[N:26]=4)[CH2:20][CH2:21]3)=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 46852697(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amine

Product 1

HCID 46853009(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-ethyl-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amine

Procedure

The title compound is prepared as a yellow solid (67 mg, 20% yield) following Scheme 3 and in analogy to Example 40 using acetaldehyde (181 μg, 3.21 mmol 5.0 eq) and (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amine (300 mg, 0.64 mmol, 1.0 eq) as starting materials.

Sources & evidence

ORD record
ord-fd9eb64e2bd842309dbc1b57d297e6e1
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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