Methyl 3-[4-(aminomethyl)phenyl]propionate → Methyl 3-(4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenyl)propanoate

HRID 733539Notes

Reaction equation

HRID 733539 reaction equation
[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=1>>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:23][CH:22]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 413297Methyl 3-[4-(aminomethyl)phenyl]propionateHCID 578413204-Dec-1-ynylbenzaldehyde

Product 1

HCID 11212289Methyl 3-(4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenyl)propanoate

Procedure

The title compound was prepared following the procedure A using 4-dec-1-ynylbenz-aldehyde and methyl 3-[4-(aminomethyl)phenyl]propanoate (purification by flash chromatography on SiO2, EtOAc/c-Hex 20/80) as a yellow oil (53%). 1H NMR (CDCl3) δ: 7.28 (d, J=8.3 Hz, 2H), 7.23-7.13 (m, 4H), 7.08 (d, J=7.9 Hz, 2H), 3.70 (s, 2H), 3.66 (s, 2H), 3.59 (s, 3H), 2.86 (t, J=8.3 Hz, 2H), 2.55 (t, J=7.2 Hz, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.56-1.46 (m, 2H), 1.43-1.31 (m, 2H), 0.86-0.76 (m, 3H). M+ (ESI): 420.4. HPLC, Rt: 4.5 min (purity: 99.5%).

Sources & evidence

ORD record
ord-f8ec982730a848bdaa55bfe36958e5ae
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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