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

HRID 1019924Notes

Reaction equation

HRID 1019924 reaction equation
[CH2:1]=O.[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][NH:14][CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]4[CH:33]=[N:32][C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[CH:29][CH:30]=5)[N:25]=4)[CH2:17][CH2:16]3)=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1>>[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][S:23][C:24]4[CH:33]=[N:32][C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[CH:29][CH:30]=5)[N:25]=4)[CH2:19][CH2:20]3)[CH3:1])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 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 66747431(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-methyl-amine

Procedure

The title compound is prepared as a yellow foam (30 mg, 29% yield) following Scheme 3 and in analogy to Example 40 using paraformaldehyde (37 mg, 0.64 mmol 3.0 eq) and (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-amine (100 mg, 0.22 mmol, 1.0 eq) as starting materials.

Sources & evidence

ORD record
ord-64d3ff8da81a42119e304644985a5031
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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