N-Methylpiperidine → 4-(2-(4-Methylpiperazin-1-yl)-2-oxoethoxy)benzaldehyde

HRID 592084Notes

Reaction equation

HRID 592084 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1)=[O:2].CN1CCCCC1.C(C1C=C(C=CC=1)OC[C:28]([N:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1)=O)=O>>[CH3:28][N:30]1[CH2:35][CH2:34][N:33]([C:9](=[O:11])[CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:13][CH:12]=2)[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 12291N-MethylpiperidineHCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 89725867Tert-Butyl 4-(2-(3-formylphenoxy)acetyl)piperazine-1-carboxylate

Product 1

HCID 283794934-(2-(4-Methylpiperazin-1-yl)-2-oxoethoxy)benzaldehydeYield 66%

Procedure

2-(4-Formylphenoxy)acetic acid (53) was treated with 1-methylpiperidine in an analogous manner to Compound 49 to afford the desired product (66%) as a colorless oil. LCMS: 99.0% (M++1).

Sources & evidence

ORD record
ord-faedc26ebb2d4a61a725f1b1aaa7de48
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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