N-(2-Aminoethyl)piperidine → HCID 59736788, compound

HRID 252838Notes

Reaction equation

HRID 252838 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[N:15]1([CH2:21][CH2:22][NH2:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)(=O)C>[N:15]1([CH2:21][CH2:22][NH:23][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 59736788HCID 59736788, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-fluorobenzoate 185 (0.502 g, 2.55 mmol) and 2-(piperidin-1-yl)ethanamine 186 (1.46 mL, 10.21 mmol) were stirred neat at 120° C. overnight then diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate (1×), brine (1×), dried over magnesium sulfate and evaporated to give 187 (0.501 g, 64%). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 7.59 (d, J=8.8 Hz, 2H), 6.55 (d, J=8.8 Hz, 2H), 6.24 (t, J=5.1 Hz, 1H), 4.11 (m, 2H), 3.21 to 3.13 (m, 6H), 2.44 (t, J=7.1 Hz, 2H), 2.37 (m, 2H), 1.49 (s, 9H), 1.47 to 1.38 (m, 2H). MS: 304.22 (calc), 249.1 (M-tBu).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (1×), brine (1×)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-3bc986c0f0794159a6b5a54a55ab59aa
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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