Potassium Iodide → HCID 10146039, compound

HRID 1977239Notes

Reaction equation

HRID 1977239 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34]Cl)=[CH:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[CH3:24])=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.[I-].[K+].C([O:47][CH2:48][CH3:49])(=O)C>CN(C=O)C>[CH2:48]([O:47][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:30][CH:31]=1)[C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=1)=[C:23]2[CH3:24])[C:49]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 86756696HCID 86756696, compound

Product 1

HCID 10146039HCID 10146039, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1.1 g (0.00953 mol) of 5benzyloxy-2-(3-benzyloxy-phenyl-1-[4-(2-chloro-ethoxy)-benzyl]-3methyl-1H-indole (example No. 58) in 10 mL of DMF was added 1.1 mL (0.0112 mol) of piperidine, and 0.93 g (00561 mol) of potassium iodide. The reaction mixture was heated to ˜40-50° C. for 4 hours. After cooling the reaction mixture to room temperature, 150 mL of ethyl acetate were added and the mixture was washed with water (3×100 mL). The organic solution was collected, washed with saturated brine, removed, dried over magnesium sulfate, filtered and evaporated to yield 1.0 g of product of the product after purification. Mp=125-126° C.; 1H NMR (DMSO) 7.48-7.45 (d, 2 H, J=7.2 Hz), 7.41-7.35 (m, 7 H), 7.33-7.28 (m, 2 H), 7.23-7.21 (d, 1 H, J=9.0 Hz), 7.13-7.12 (d, 1 H, J=2.4 Hz), 7.06-7.03 (m, 1 H), 6.95-6.91 (m, 2 H), 6.83-6.80 (dd, 1 H, J=2.4 Hz, J=6.3 Hz), 6.75-6.70 (m, 4 H), 5.13 (s, 2 H), 5.11 (s, 2 H), 5.02 (s, 2 H), 3.93-3.90 (t, 2 H, J=6.0 Hz), 2.56-2.53 (t, 2 H, J=5.9 Hz), 2.49-2.48 (m, 4 H), 2.14 (s, 3 H), 1.46-1.40 (m, 4 H), 1.35-1.31 (m, 2 H); IR (KBr) 3400, 2900 cm−1; MS eI m/z 636 (M+); CHN calcd for C43H44H2O3+0.25 H2O.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. washthe mixture was washed with water (3×100 mL)
  3. customThe organic solution was collected
  4. washwashed with saturated brine
  5. customremoved
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0a27afeadfb34e83b52f2d0b87766e42
Source dataset
uspto-grants-2001_05
Patent number
US06232307B1

Reaction notes

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