Trifluoroacetic acid → 4-(4-Aminomethylpiperidin-1-ylmethyl)-piperidine-1-carboxylic acid methyl ester

HRID 1098344Notes

Reaction equation

HRID 1098344 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:19]C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][NH2:19])[CH2:16][CH2:17]2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668109034-[4-(Tert-butoxycarbonylamino-methyl)piperidin-1-ylmethyl]-piperidine-1-carboxylic acid methyl ester

Product 1

HCID 668107854-(4-Aminomethylpiperidin-1-ylmethyl)-piperidine-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(tert-butoxycarbonylamino-methyl)piperidin-1-ylmethyl]-piperidine-1-carboxylic acid methyl ester (4.4 g, 10.8 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (20 mL). After stirring for 20 min at room temperature, the solution was evaporated in vacuo, yielding the bis-trifluoroacetate salt of the title compound as a pale yellow oil, which was used without further treatment. (m/z): [M+H]+ calcd for C14H27N3O2 270.22; found 270.5. 1H-NMR (CD3OD) δ (ppm) 4.0 (br d, 2H), 3.6 (m, 5H), 2.9-2.7 (m, 6H), 2.1-1.9 (m, 2H), 1.7-1.5 (m, 6H), 1.2-1.0 (m, 4H).

Workup

  1. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-b8977ab313a04162b3a7eae26b1e7093
Source dataset
uspto-grants-2012_03
Patent number
US08143279B2

Reaction notes

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