Ammonia → 4-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}-butyramide

HRID 1097290Notes

Reaction equation

HRID 1097290 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:25](=[O:26])[CH:24]3[CH:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)[C:18]2=[O:27])[CH2:9][CH2:8]1.[NH3:29]>>[O:27]=[C:18]1[CH:19]2[CH:24]([CH:23]=[CH:22][CH:21]=[CH:20]2)[C:25](=[O:26])[N:17]1[CH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:7]([CH2:6][CH2:5][CH2:4][C:3]([NH2:29])=[O:2])[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 668112194-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}butyric acid methyl ester

Product 1

HCID 668109714-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}-butyramideYield 40%

Conditions

Temperature
70 °C

Procedure

A solution containing 7.0 M methanolic ammonia (50 mL) and compound 3 (0.90 g, 2.33 mmol) was heated in a sealed tube at 70° C. for 72 hours. The solution was then cooled to ambient temperature, and concentrated under vacuum. The resulting residue was subjected to column chromatography eluting with 0-3% methanol in dichloromethane to afford the desired product 4 (0.5 g, 40%) as a colorless, viscous oil: 1H NMR (300 MHz, CDCl3) δ 1.25 (m, 3H), 1.55 (m, 2H), 1.62-1.80 (m, 4H), 1.90 (m, 2H), 2.18 (t, 2H), 2.34 (t, 2H), 2.90 (d, 2H) 3.68 (s, 3H), 5.40 (br, 2H), 7.68 (d, 2H), 7.82 (d, 2H).

Workup

  1. temperatureThe solution was then cooled to ambient temperature
  2. concentrationconcentrated under vacuum
  3. washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-a1d852d4d3f14fb8a84a79f4274fd10b
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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