Ammonia → 2-(((2-Aminoethyl)(3-(4-benzylpiperidin-1-yl)propyl)amino)methyl)phenol

HRID 403134Notes

Reaction equation

HRID 403134 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35]C(C)(C)C)[CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>CO>[NH2:20][CH2:19][CH2:18][N:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35])[CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 70896359Tert-butyl 2-((3-(4-benzylpiperidin-1-yl)propyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

Product 1

HCID 498501482-(((2-Aminoethyl)(3-(4-benzylpiperidin-1-yl)propyl)amino)methyl)phenolYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same procedure as described for compound L24a was applied to compound 26 (0.7 g, 1.3 mmol) Purification was carried out on a silica gel TLC plate that was developed in with a 6% methanolic NH3 (7 M NH3 in methanol/94% CH2Cl2. The product was isolated as pale yellow oil (60%). 1H NMR (CDCl3) δ 7.257 (t, 2H, Ar), 7.163 (m, 2H, Ar), 7.118 (d, 2H, Ar), 6.952 (d, 1H, Ar), 6.801 (d, 1H, Ar), 6.757 (t, 1H, Ar), 3.724 (s, 2H, —CH2—), 2.867 (q, 4H, —CH2—CH—), 2.553 (m, 4H, —CH2—CH2—), 2.511 (d, 2H, —CH2—), 2.278 (t, 2H, —CH2—), 1.837 (ddd, 2H, —CH2—), 1.725 (p, 2H, —CH2—), 1.608 (d, 2H, —CH2—), 1.500 (m, 1H, —CH—), 1.275 (m, 2H, —CH2—). Mass Spec.=382.29 (M+H)+.

Sources & evidence

ORD record
ord-6aa25590264449dca6db770a4eecf32b
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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