1,2-Dibromoethane → N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidine

HRID 887949Notes

Reaction equation

HRID 887949 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][C:11](=[O:16])[CH2:10][C:9]2([CH3:18])[CH3:17])CCC[CH2:3][CH2:2]1.BrCCBr.ICCC.C([Cu])#N.[Li+].[Cl-].CC1(C)N([O])C(C)(C)CC(=O)C1>[Zn].C[Si](C)(C)Cl>[CH2:1]([O:7][N:8]1[C:9]([CH3:18])([CH3:17])[CH2:10][C:11](=[O:16])[CH2:12][C:13]1([CH3:14])[CH3:15])[CH2:2][CH3:3]

Participants

9

Reactant 6

HCID 78391,2-DibromoethaneHCID 336431-IodopropaneHCID 433294Lithium ChlorideHCID 520789TemponeHCID 22019868N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidineHCID 178418546HCID 178418546, compound

Product 1

HCID 23450603N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidineYield 26%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6397ChlorotrimethylsilaneSolvent

Procedure

N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidine (3.2 g, 26%) is synthesized in the same manner as described above with regard to N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine, with the exception of the addition of Zn (61.1 mmol, 4.00 g), 1,2-dibromoethane (200 μl), trimethyl-chlorosilane (250 μl), iodopropane (58.8 mmol, 10.0 g), CuCN (53.6 mmol, 4.80 g), LiCl (114 mmol, 4.80 g) and 4-oxo-TEMPO (58.8 mmol, 10.0 g). 1H-NMR (CDCl3): δ=3.78 (t, J=6.7 Hz, 2H, O—CH2), 2.55 (d, J=12.7 Hz, 2H, CH2—CCH3), 2.20 (d, J=12.7 Hz, 2H, CH2—CCH3), 1.57 (m, 2H, CH2—CH3), 1.28 (s, 6H, C—CH3), 1.14 (s, 6H, C—CH3), 0.95 (t, J=7.45 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3): δ208.5, 78.5, 63.0, 53.3, 32.5, 22.5, 21.8, 10.9.

Sources & evidence

ORD record
ord-9eff13ac34ea49b8a1727c816fcf7374
Source dataset
uspto-grants-2012_08
Patent number
US08247479B2

Reaction notes

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