Methyl 4-(aminomethyl)benzoate hydrochloride → Methyl 4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]benzoate

HRID 733590Notes

Reaction equation

HRID 733590 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]>>[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]2[CH:33]=[CH:32][C:29]([CH2:30][NH:2][CH2:3][C:4]3[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=3)=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehyde

Product 1

HCID 11475414Methyl 4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]benzoate

Procedure

The titled compound was prepared following the procedure A using methyl 4-(aminomethyl)benzoate hydrochloride and 4-[(4-butylphenyl)ethynyl]benzaldehyde as a white solid (54%). 1H NMR (CDCl3, 300 MHz) δ 8.02 (d, J=8.3 Hz, 2H), 7.51 (d, J=7.9 Hz, 2H), 7.44 (m, 4H), 7.33 (d, J=7.9 Hz, 2H), 7.17 (d, J=7.9 Hz, 2H), 3.92 (s, 3H), 3.87 (s, 2H), 3.82 (s, 2H), 2.63 (t, J=7.7 Hz, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, J=7.3 Hz, 3H). M+ (ESI): 412.4. HPLC, Rt: 4.28 min (Purity: 99.4%).

Sources & evidence

ORD record
ord-4c2bc1a06857407590e08a46bd076ac9
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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