Sodium Iodide → HCID 60078709, compound

HRID 1832201Notes

Reaction equation

HRID 1832201 reaction equation
[CH3:1][CH:2]([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=1)=[O:4].Cl[CH2:20][CH2:21][C@H:22]([O:29][C:30]1(OC2C=CC=CC=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:43](=[O:46])([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[CH3:1][CH:2]([CH3:18])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][C@H:22]([O:29][C:30]3[CH:31]=[CH:32][C:33]([O:46][C:43]4[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=4)=[CH:34][CH:35]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:14][CH2:13]2)[CH:7]=1)=[O:4]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 167572552-methyl-N-[3-(4-piperidyl)phenyl]propanamideHCID 69523623HCID 69523623, compound

Product 1

HCID 60078709HCID 60078709, compoundYield 149.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (65.5 mg, 0.266 mmol), 4-{[(1S)-3-chloro-1-phenylpropyl]oxy}-(4-phenoxy)benzene (0.100 mg, 0.296 mmol), potassium carbonate (40.9 mg, 0.296 mmol) and sodium iodide (67.0 mg, 0.444 mmol) in DMF (1.0 mL) at 100° C. for 3 hours. The reaction mixture was poured into water (50 mL) and the aqueous layer was extracted with methylene chloride (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by Prep-TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3] to give the desired product (0.109 g, 74.6%) as a thick oil: 1H NMR (400 MHz, CDCl3) δ 7.48 (s, 1H), 7.40–7.30 (m, 4H), 7.20–7.10 (m, 6H), 7.09 (s; 1H), 6.99 (apparent d, 1H, J=7.8 Hz), 6.98 (apparent t, 1H, J=7.8 Hz), 6.93 (apparent d, 2H, J=8.4 Hz), 6.84 (m, 2H), 5.20 (apparent dd, 1H, J=4.4, 8.5 Hz), 3.03 (m, 2H), 2.51 (m, 4H), 2.24 (apparent sept, 1H, J=7.8 Hz), 2.20–2.10 (m, 3H), 1.90 (m, 4H), 1.25 (d, 6H, J=7.9 Hz); ESMS m/e: 549.41 (M+H)+; Anal. Calc. for C36H40N2O3: C, 78.80; H, 7.35; N, 5.11. Found: C, 78.58; H, 7.48; N, 5.09.

Workup

  1. extractionthe aqueous layer was extracted with methylene chloride (3×30 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by Prep-TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3]

Sources & evidence

ORD record
ord-4c029fd8e7654a5b917a1e4b0c5b78e5
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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