Diisopropylethylamine → Methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl]phenoxy)acetate

HRID 733527Notes

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].C(O)(=O)C.[NH2:23][CH2:24][C:25]1[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C>>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:23][CH2:24][C:25]2[CH:36]=[CH:35][C:28]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=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

Reactant 3

HCID 81531Diisopropylethylamine

HCID 578413204-Dec-1-ynylbenzaldehyde

HCID 86028338Methyl [4-(aminomethyl)phenoxy]acetate acetate

Product 1

HCID 57841392Methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl]phenoxy)acetate

Procedure

The title compound was prepared following the procedure A using 4-dec-1-ynylbenzaldehyde, methyl [4-(aminomethyl)phenoxy]acetate, acetate salt and DIEA (1 eq.) (purification by flash chromatography on SiO2, DCM/MeOH 95:5) as a pale yellow oil (63%). M+ (ESI): 422.2. HPLC, Rt: 4.3 min (purity: 96.4%). 1H NMR (CDCl3) δ: 7.37 (d, J=8.3 Hz, 2H), 7.28 (m, 4H), 6.88 (d, J=8.6 Hz, 2H), 4.63 (s, 2H), 3.78 (m, 7H), 2.40 (t, J=7.0 Hz, 2H), 1.61 (m, 2H), 1.44 (m, 2H), 1.30 (brs, 8H), 0.90 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record: ord-ceba55eb319249608e6c5506f096373c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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