trans-N-Boc-2-(1-pentenyl)-6-methylpiperidine → trans-2-(1-Pentenyl)-6-methylpiperidine

HRID 1919728Notes

Reaction equation

HRID 1919728 reaction equation
C([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:15]=[CH:16][CH2:17][CH2:18][CH3:19])(OC(C)(C)C)=O>FC(F)(F)C(O)=O.ClCCl>[CH:15]([C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([CH3:14])[NH:8]1)=[CH:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 67498452trans-N-Boc-2-(1-pentenyl)-6-methylpiperidine

Product 1

HCID 67498979trans-2-(1-Pentenyl)-6-methylpiperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of trans-N-Boc-2-(1-pentenyl)-6-methylpiperidine (2.5 g, 9.35 mmol) in 15% trifloroacetic acid (35 mL) in dichloromethane was stirred for 2 h at room temperature, and the reaction mixture was quenched with 90 mL saturated NaHCO3 solution. The mixture was extracted with ether *5 and the combined extracts were dried over K2CO3 and then concentrated to give trans-2-(1-pentenyl)-6-methylpiperidine as an oil. The crude oil was immediately dissolved in a small amount of ether, and ether saturated with HCl (g) was added slowly via pipette. This solution was allowed to stand for 10 minutes, and the solvent was evaporated. More ether was added and the flask was swirled constantly until crystallization occurred. The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid that was homogeneous by TLC analysis. mp 150.4-150.9° C.; 1H NMR (250 MHz) δ 9.5-9.3 (br. d, 2H), 5.74-5.62 (m, 2H), 4.19 (s, 1H), 3.55 (s, 1H), 2.1-1.3 (m, 13H), 0.87 (t, 3H); 13C NMR (62.7 MHz) δ 136.8 (s), 123.0 (s), 48.3 (s), 47.9 (s), 29.9 (s), 28.8 (s), 28.4 (s), 22.3 (s), 17.6 (s), 17.1 (s), 13.8 (s). FT-IR (neat): 3424, 3171, 2939, 1635, 1597, 1582, 1459, 1432, 1384, 1287, 1123, 1075, 895. Elemental Analysis for C11H22NCl: C, 64.83%; H, 10.9%; N, 6.87%. Found: C, 64.77%; H, 10.82%; N, 6.85%.

Workup

  1. customthe reaction mixture was quenched with 90 mL saturated NaHCO3 solution
  2. extractionThe mixture was extracted with ether *5
  3. dry with materialthe combined extracts were dried over K2CO3
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7333f6dae74f4fd29331a71801677fae
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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