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

HRID 887950Notes

Reaction equation

HRID 887950 reaction equation
[CH2:1]([O:4][N:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8](=O)[CH2:7][C:6]1([CH3:15])[CH3:14])[CH2:2][CH3:3].C([O-])(=O)C.[NH4+].[BH3-]C#[N:23].[Na+]>>[NH2:23][CH:8]1[CH2:9][C:10]([CH3:12])([CH3:11])[N:5]([O:4][CH2:1][CH2:2][CH3:3])[C:6]([CH3:15])([CH3:14])[CH2:7]1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 23450603N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidine

Product 1

HCID 234505994-Amino-N-propoxy-2,2,6,6-tetramethylpiperidineYield 62%

Procedure

4-Amino-N-propoxy-2,2,6,6-tetramethylpiperidine (1.6 g, 62%) is prepared from N-propoxy-4-oxo-2,2,6,6-tetramethylpiperidine (12.2 mmol, 2.60 g) by the same method as described above, with the exception of the addition of ammonium acetate (122 mmol, 9.40 g), 6 g molecular sieves (10−10 m) and 95% NaBH3CN (12.2 mmol, 0.8 g). 1H-NMR (CDCl3); δ=3.61 (t, J=6.6 Hz, 2H, CH2—O), 2.99 (m, 1H, NH2—CH), 1.58 (d, J=11.4 Hz, 2H, NH2), 1.46 (m, 2H, CH2—CH3), 1.20 (m, 4H), 1.16 (s, 6H, CH3), 1.13 (s, 6H, CH3), 0.93 (t, J=7.4 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3): δ=78.3, 59.8, 49.9, 41.4, 33.2, 21.9, 20.9, 10.9.

Sources & evidence

ORD record
ord-89b46945bd04428c872bcdbe320998f3
Source dataset
uspto-grants-2012_08
Patent number
US08247479B2

Reaction notes

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