Ammonium Acetate → 4-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 887952Notes

Reaction equation

[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=O)[CH2:12][C:11]1([CH3:20])[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])(=O)C.[NH4+].[BH3-]C#[N:28].[Na+]>>[NH2:28][CH:13]1[CH2:14][C:15]([CH3:17])([CH3:16])[N:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:11]([CH3:20])([CH3:19])[CH2:12]1

Participants

Reactant 3

HCID 517165Ammonium Acetate

HCID 5003444Sodium cyanoborohydride

HCID 22019882N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

Product 1

HCID 233720934-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidineYield 62%

Procedure

4-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine (16.7 g, 62%) is prepared from N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine (95.4 mmol, 27.0 g) by the same method as described above, with the exception of the addition of ammonium acetate (954.5 mmol, 73.5 g), 15 g molecular sieves (10−10 m) and 95% NaBH3CN (95.4 mmol, 6.32 g). 1H-NMR (CDCl3); δ=3.61 (t, J=6.6 Hz, 2H, CH2—O), 2.99 (m, 1H, NH2—CH), 1.63 (d, J=11.4 Hz, 2H, NH2), 1.46 (m, 4H, CH2—CH3), 1.26 (m, 12H), 1.15 (s, 6H, CH3), 1.12 (s, 6H, CH3), 0.87 (t, J=7.4 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3): δ=77.0, 59.8, 50.1, 41.4, 33.2, 31.8, 29.6, 29.2, 28.6, 26.4, 21.3, 21.4, 14.1.

Sources & evidence

ORD record: ord-e4a85afddb3e47179621f0d4d6203a7f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247479B2

Reaction notes

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