Sodium Iodide → HCID 17956100, compound

HRID 2103268Notes

Reaction equation

HRID 2103268 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15].[CH2:16]([O:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC#N>[CH2:16]([O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][C:6]2=[O:15])[CH2:22][CH2:21]1)[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 114920374-PropoxypiperidineHCID 16782057HCID 16782057, compound

Product 1

HCID 17956100HCID 17956100, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A 4 mL vial was charged with crude 1-(3-chloro-propyl)-3,4-dihydro-1H-quinolin-2-one (85LM31) (0.200 g), 4-propoxy-piperidine (79KS-66) (0.130 g, 0.897 mmol), potassium carbonate (0.247 g, 1.79 mmol) and sodium iodide (0.269 g, 1.79 mmol) in MeCN (2 mL) and shaken at 50° C. for 20 h. The reaction mixture was quenched with water (1 mL), and the product was extracted into EtOAc (3×1 mL). The combined organic layers were dried over Na2SO4, evaporated and purified by flash CC (SiO2; MeOH/DCM 0:1→3:7) to give the title compound (85LM32) (0.012 g, total yield 3%). 1H NMR (CDCl3) δ 7.25 (t, J=7.4 Hz, 1H), 7.18-7.08 (m, 2H), 6.98 (t, J=7.4 Hz, 1H), 3.98 (t, J=7.6 Hz, CH2), 3.38 (t, J=6.8 Hz, CH2), 3.35-3.25 (m, 1H), 2.87 (t, J=7.6 Hz, CH2), 2.80-2.70 (m, 2H), 2.65-2.60 (m, 2H), 2.45-2.35 (m, 2H), 2.20-2.10 (m, 2H), 1.95-1.80 (m, 4H), 1.65-1.50 (m, 4H), 0.95 (t, J=7.6 Hz, CH3); 13C NMR (CDCl3) δ 170.2, 140.0, 128.2, 127.5, 126.6, 122.8, 115.3, 70.0, 56.0, 51.8, 40.5, 32.0, 31.5, 25.8, 25.2, 22.8, 10.7; HPLC-MS (ammonium acetate) [M+H]+=331.3.

Workup

  1. customThe reaction mixture was quenched with water (1 mL)
  2. extractionthe product was extracted into EtOAc (3×1 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. custompurified by flash CC (SiO2; MeOH/DCM 0:1→3:7)

Sources & evidence

ORD record
ord-fc490600bd6946f2b1228543c5dcd81b
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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