trans-N-Boc-2-isohexyl-6-methylpiperidine → trans-2-Isohexyl-6-methylpiperidine

HRID 840698Notes

Reaction equation

HRID 840698 reaction equation
C([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])(OC(C)(C)C)=O>FC(F)(F)C(O)=O.ClCCl>[CH2:15]([C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([CH3:14])[NH:8]1)[CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 67499496trans-N-Boc-2-isohexyl-6-methylpiperidine

Product 1

HCID 67498965trans-2-Isohexyl-6-methylpiperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of trans-N-Boc-2-isohexyl-6-methylpiperidine (1.4 g, 5.50 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-isohexyl-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 occured. The solid was collected via filtration, and dried in vacuo to give the piperidinium hydrochloride as a white solid. mp 155.0-156.0° C.; 1H NMR (250 MHz) δ9.17 (s, 2H), 3.50 (s, 1H), 3.25 (s, 1H), 1.94-1.15 (m, 16H), 0.82 (d, 6H); 13C NMR (62.7 MHz) δ51.7 (s), 47.9 (s), 38.4 (s), 30.9 (s), 28.8 (s), 27.8 (s), 26.1 (s), 23.5 (s), 22.5 (s), 22.3 (s), 17.3 (s), 16.8 (s) ppm. FT-IR (neat): 3430, 2948, 1615, 1589, 1557, 1472, 1436, 1418, 1362, 1102, 895. Elemental Analysis for C12H26NCl: C, 65.56%; H, 11.95%; N, 6.37%. Found: C, 64.90%; H, 11.89%; N, 6.26%.

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-4e28c737047f4a47a35a501380e13e4d
Source dataset
uspto-grants-2002_04
Patent number
US06369078B1

Reaction notes

Loading…