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

HRID 2356775Notes

Reaction equation

HRID 2356775 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-3a0d4f63cd774b6cb2423a179606b3d9
Source dataset
uspto-grants-2010_07
Patent number
US07759363B2

Reaction notes

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