2-Amino-2-phenylethanol → N-dodecyl-4-{[(2-hydroxy-1-phenylethyl)amino]methyl}benzamide

HRID 735923Notes

Reaction equation

[CH2:1]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:24][CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:26][OH:27]>>[CH2:1]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:24][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][OH:27])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Reactant 2

HCID 924662-Amino-2-phenylethanol

HCID 86598530HCID 86598530, compound

Product 1

HCID 67187582N-dodecyl-4-{[(2-hydroxy-1-phenylethyl)amino]methyl}benzamideYield 83%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using N-dodecyl-4-formylbenzamide and 2-amino-2-phenylethanol gave the title compound as a white powder (83%). 1H NMR (CD3OD, 300 MHz) δ 7.79 (d, J=8.3 Hz, 2H), 7.44-7.26 (m, 7H), 3.85-3.56 (m, 5H), 3.39 (t, J=7.2 Hz, 2H), 1.71-1.58 (m, 2H), 1.47-1.25 (m, 18H), 0.92 (t, J=6.8 Hz, 3H) M−(LC/MS(ESI)): 437.5; M+(LC/MS(ESI)): 439.6 HPLC (Condition A), Rt: 4.26 min (HPLC purity: 98.8%).

Workup

customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record: ord-fa8d3c16d1c14ecf902d7a98cd5ca7ca
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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