3-Phenoxybenzoic acid → N-(5-Hydroxymethyl-adamantan-2-yl)-3-phenoxy-benzamide

HRID 2194645Notes

Reaction equation

HRID 2194645 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][CH:18]1[CH:25]2[CH2:26][C:21]3([CH2:28][OH:29])[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)[CH2:24]2>>[OH:29][CH2:28][C:21]12[CH2:20][CH:19]3[CH2:27][CH:23]([CH2:24][CH:25]([CH:18]3[NH:17][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[CH2:26]1)[CH2:22]2

Participants

3

Reactant 2

HCID 195393-Phenoxybenzoic acidHCID 579281674-Aminotricyclo[3.3.1.13,7]decane-1-methanol

Product 1

HCID 25108929N-(5-Hydroxymethyl-adamantan-2-yl)-3-phenoxy-benzamide

Procedure

Prepared from 3-phenoxy benzoic acid and 4-amino-1-hydroxymethyladamantane to give the title compound as a mixture of two isomers. 1H NMR (400 MHz, CDCl3) δ: 7.31-7.49 (m, 5H), 7.08-7.18 (m, 2H), 7.02 (d, 2H), 6.29-6.43 (m, 1H), 4.13-4.23 (m, 1H), 3.24 (d, 2H), 2.09-2.18 (m, 2H), 2.01 (br. s., 1H), 1.55-1.92 (m, 10H), 1.44 (d, 1H).

Sources & evidence

ORD record
ord-abf0a006e801412c9e3a2ca4ee59e3e5
Source dataset
uspto-grants-2012_12
Patent number
US08334305B2

Reaction notes

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