Hydrazine hydrate (1:1) → 1-{4-[2-(Aminooxy)ethyl]piperidin-1-yl}hexadecan-1-one

HRID 2112424Notes

Reaction equation

HRID 2112424 reaction equation
O.NN.[C:4]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][O:29][N:30]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:23][CH2:22]1)(=[O:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(O)C>[NH2:30][O:29][CH2:28][CH2:27][CH:24]1[CH2:25][CH2:26][N:21]([C:4](=[O:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57642037HCID 57642037, compound

Product 1

HCID 576420431-{4-[2-(Aminooxy)ethyl]piperidin-1-yl}hexadecan-1-oneYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.14 ml, 2.96 mmol) was added to a solution of 2-[2-(1-(hexadecanoyl)piperidin-4-yl)ethoxy]isoindole-1,3-dione (1.52 g, 2.96 mmol) in ethanol (30 ml). The reaction mixture was heated to reflux for 75 min and cooled to room temperature. The formed precipitation was removed by filtration. The solvent of the filtrate was removed in vacuo. The crude product was purified by flash chromatography on silica (30 g), using a mixture of dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 800 mg of 1-[4-(2-(aminooxy)ethyl)piperidin-1-yl]hexadecan-1-one.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 75 min
  3. customThe formed precipitation
  4. customwas removed by filtration
  5. customThe solvent of the filtrate was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (30 g)
  7. additiona mixture of dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent

Sources & evidence

ORD record
ord-771be3429165410dbed4cc2d2a919cd8
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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