HCID 67498983, compound → HCID 67498472, compound

HRID 1919738Notes

Reaction equation

HRID 1919738 reaction equation
C([N:8]1[C@@H:13]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH3:20])(OC(C)(C)C)=O>FC(F)(F)C(O)=O.ClCCl>[CH3:20][C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[NH:8]1

Participants

4

Reactant 1

HCID 67498983HCID 67498983, compound

Product 1

HCID 67498472HCID 67498472, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of trans-N-Boc-2-methyl-6-(ethenyl propionyl)piperidine. (1.8 g, 3.36 mmol) in 15% trifloroacetic acid (35 mL) in dichloromethane was stirred for 2 h at room temperature, and the reaction mixture was quenched with 75 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-methyl-6-(ethenyl propionyl)piperidine 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. mp 154.8-156.3; 1H NMR (300 MHz) δ 9.89 (s, 2H), 7.03 (dd, 1H), 6.24 (d, 1H), 4.24-4.11 (m, 3H), 3.45 (s, 1H), 2.2-1.49 (m, 9H), 1.26-1.22 (t, 3H); 13C NMR (75 MHz) 6165.1 (s), 140.1 (s), 126.3 (s), 60.83 (s), 54.3 (s), 51.8 (s), 48.6 (s), 29.4 (s), 27.9 (s), 26.3 (s), 17.9 (s), 14.1 (s) ppm. FT-IR (neat): 3374, 3107, 2943, 1717, 1683, 1635, 1539, 1436, 1312, 1190, 1033, 981. Elemental Analysis for C11H20NO2Cl: C, 56.52%; H, 8.64%; N, 5.99%. Found: C, 56.37%; H, 8.58%; N, 5.89%.

Workup

  1. customthe reaction mixture was quenched with 75 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-8c4f4d0d79cd4bddb9f59abc1f6803eb
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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