Potassium Carbonate → HCID 9899559, compound

HRID 1168842Notes

Reaction equation

HRID 1168842 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH3:11][O:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:11][O:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][N:8]1[CH2:9][CH2:10][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 132838674-Butylpiperidine

Product 1

HCID 9899559HCID 9899559, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 50 mL flask was charged with a mixture of 3 (2.7 g, 15 mmol), 4-bromo butyric acid methyl ester (9.9 g, 55 mmol) and potassium carbonate (8.6 g, 62 mmol) in acetonitrile (25 mL). The mixture was stirred at room temperature for 72 hours followed by evaporation to dryness. The crude product was subjected to column chromatography (eluent: CH2Cl2:CH3OH (96:4)) to produce pure 4 (3.4 g, 94%). 1H NMR (CDCl3) δ0.89 (t, 3H), 1.20-1.39 (m, 9H), 1.69 (d, 2H), 1.89 (qv, 2H), 1.98 (t, 2H), 2.36 (t, 2H), 2.43 (t, 2H), 3.99 (d, 2H), 3.67 (s, 3H).

Workup

  1. customfollowed by evaporation to dryness

Sources & evidence

ORD record
ord-8a31526e5e3241868086d4526557c734
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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