Chlorotrimethylsilane → N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

HRID 887951Notes

Reaction equation

HRID 887951 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])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)Cl.I[CH2:25][CH2:26]CCCCCC.C([Cu])#N.[Li+].[Cl-].CC1(C)N([O])C(C)(C)CC(=O)C1>[Zn].BrCCBr>[CH2:1]([O:7][N:8]1[C:9]([CH3:17])([CH3:18])[CH2:10][C:11](=[O:16])[CH2:12][C:13]1([CH3:14])[CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:25][CH3:26]

Participants

9

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 123801-IodooctaneHCID 433294Lithium ChlorideHCID 520789TemponeHCID 22019868N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidineHCID 178418546HCID 178418546, compound

Product 1

HCID 22019882N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidineYield 36%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 78391,2-DibromoethaneSolvent

Procedure

N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine (30.3 g, 36%) is synthesized in the same manner as described above with regard to N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethyl-piperidine, with the exception of the addition of Zn (294.0 mmol, 19.25 g), 1,2-dibromoethane (900 μl), trimethylchlorosilane (1.2 ml), iodooctane (294 mmol, 70.6 g), CuCN (294 mmol, 26.3 g), LiCl (588 mmol, 25.0 g) and 4-oxo-TEMPO (294 mmol, 50.0 g). 1H-NMR (CDCl3): δ=3.69 (t, J=6.5 Hz, 2H, O—CH2), 2.55 (d, J=12.8 Hz, 2H, CH2—CCH3), 2.20 (d, J=12.8 Hz, 2H, CH2—CCH3), 1.54 (m, 2H, CH2—CH3), 1.36 (m, 2H, CH2), 1.28 (m, 14H, CH2 and C—CH3), 1.15 (s, 6H, C—CH3), 0.88 (t, J=6.8 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3) δ=208.4, 77.1, 62.9, 53.3, 32.5, 31.8, 29.6, 29.2, 28.6, 26.4, 22.6, 22.5, 14.1.

Sources & evidence

ORD record
ord-182e11e89aad446ab6961444dfdb91aa
Source dataset
uspto-grants-2012_08
Patent number
US08247479B2

Reaction notes

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