Hydrochloric Acid → HCID 86690242, compound

HRID 80747Notes

Reaction equation

HRID 80747 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][C:4]1([CH3:17])[CH3:16].[ClH:18].O1CCOCC1>CCOCC>[Cl-:18].[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][NH2+:6][CH2:5][C:4]1([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71244823(S)-tert-butyl 4-methoxy-3,3-dimethylpiperidine-1-carboxylate

Product 1

HCID 86690242HCID 86690242, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To neat (S)-tert-butyl 4-methoxy-3,3-dimethylpiperidine-1-carboxylate (5.87 g, 24.1 mmol) was added 4.0 M HCl in dioxane (24.1 mL, 96.0 mmol), and the reaction mixture was stirred at room temperature for 16 h. Then, the reaction mixture was diluted with heptanes (60 mL) and Et2O (10 mL) and stirred at room temperature until a white solid crashed out. The heterogeneous mixture was then filtered and the white solid was collected to afford (S)-4-methoxy-3,3-dimethylpiperidin-1-ium chloride. 1H NMR (400 MHz, CDCl3) δ ppm 9.58 (br. s., 1 H), 9.23 (br. s., 1 H), 3.34 (s, 3 H), 3.09-3.24 (m, 2 H), 3.05 (t, J=10.0 Hz, 1 H), 2.97 (dd, J=5.4, 2.4 Hz, 1 H), 2.76 (d, J=13.1 Hz, 1 H), 2.04-2.17 (m, 1 H), 1.84-1.96 (m, 1 H), 1.19 (s, 3 H), 1.05 (s, 3 H).

Workup

  1. stirringstirred at room temperature until a white solid
  2. filtrationThe heterogeneous mixture was then filtered
  3. customthe white solid was collected

Sources & evidence

ORD record
ord-bd727c7f910a4b77a83605bae975cfd0
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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