Acetic Acid → 4-[1-(4-Aminobutyl)piperidin-4-yl]butyramide

HRID 1097291Notes

Reaction equation

HRID 1097291 reaction equation
O=C1C2C(C=CC=C2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:18][CH2:17]1.O.NN.C(O)(=O)C>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 668109714-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}-butyramide

Product 1

HCID 668109774-[1-(4-Aminobutyl)piperidin-4-yl]butyramideYield 130.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 4 (0.30 g, 0.76 mmol) was dissolved in ethanol (5 mL). To the solution was added hydrazine monohydrate (0.11 mL, 2.28 mmol) followed by a catalytic amount of acetic acid (0.1 mL). The mixture was heated to reflux for two hours, cooled to room temperature, and concentrated under vacuum. The resulting residue was subjected to column chromatography eluting with 0-20% (20:80 ammonium hydroxide/methanol) in dichloromethane to afford the desired product 5 (0.24 g, 80%) as a colorless, viscous oil: 1H NMR (500 MHz, CD3OD) δ 1.25 (m, 4H), 1.55 (m, 6H), 1.72 (m, 2H), 2.00 (m, 2H), 2.18 (m, 3H), 2.36 (t, 2H), 2.74 (t, 2H), 2.96 (d, 2H), 3.28 (br, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for two hours
  3. concentrationconcentrated under vacuum
  4. washeluting with 0-20% (20:80 ammonium hydroxide/methanol) in dichloromethane

Sources & evidence

ORD record
ord-2638c911c22a422f9465bb1e3e5b8faf
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

Loading…