Sodium Iodide → 3-(Piperidin-1-yl)propyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335539

Reaction equation

HRID 335539 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26]Cl)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH:28]1[CH2:33][CH2:32]O[CH2:30][CH2:29]1.[I-].[Na+].[CH3:36]N(C)C=O>>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][CH2:26][N:28]2[CH2:33][CH2:32][CH2:36][CH2:30][CH2:29]2)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8083MorpholineHCID 668698443-Chloropropyl 5-(tetradecyloxy)furan-2-carboxylate

Product 1

HCID 668696673-(Piperidin-1-yl)propyl 5-(tetradecyloxy)furan-2-carboxylate

Conditions

Temperature
55 °C

Procedure

To a solution of the above prepared 3-chloropropyl 5-(tetradecyloxy)furan-2-carboxylate (0.272 g, 0.68 mmol) in 6 mL of N,N-dimethylformamide was added morpholine (0.535 mL, 6.1 mmol) and sodium iodide (10 mg). The resulting solution was stirred at 55° C. for 36 hrs at which time HPLC analysis of the reaction mixture indicated near complete consumption of the starting material. The solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases were clear solutions. The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The crude material was purified by flash chromatography eluting with 5-40% EtOAc in hexanes to yield 0.217 g of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.10 (d, 1H), 5.30 (d, 1H), 4.30 (t, 2H), 4.10 (t, 2H), 3.7 (t, 4H), 2.40-2.50 (m, 6H), 1.90 (p, 2H), 1.76 (p, 2H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

Workup

  1. customindicated near complete consumption of the starting material
  2. additionThe solution was diluted with EtOAc (30 mL), brine (10 mL) and water (10 mL) such that both phases
  3. customThe phases were separated
  4. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with 5-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-2fe6932a475d47c1a1183bf39bc896bc
Source dataset
uspto-grants-2014_11
Patent number
US08884034B2

Linked notes

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