Potassium Iodide → HCID 59837458, compound

HRID 272993Notes

Reaction equation

HRID 272993 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O>[CH3:20][N:19]([CH3:21])[CH2:18][C:12]1([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)=[CH:7][CH:8]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 68576119HCID 68576119, compound

Product 1

HCID 59837458HCID 59837458, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-{4-[4-(3-chloropropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-N,N-dimethylmethanamine (200 mg, 0.7 mmol), N-methyl piperazine (87 μl, 0.79 mmol), solid sodium bicarbonate (66 mg, 0.79 mmol) and a catalytic amount of potassium iodide was heated at 50° C. in N,N-dimethylformamide (2 ml) for 18 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (2×75 ml) and water (20 ml). The organic layers were combined, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 by volume) to provide the title compound (102 mg, 39%). 1H NMR (400 MHz, CDCl3) δ 1.84-1.91 (m, 2H), 1.95-1.99 (m, 8H), 2.07-2.11 (m, 2H), 2.30 (s, 3H), 2.40 (s, 2H), 2.42-2.59 (m, 10H), 3.54 (t, 2H), 3.72-3.78 (m, 2H), 4.00 (t, 2H), 6.86 (d, 2H), 7.20 (d, 2H). HRMS ESI+ m/z 376.2951 [MH]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (2×75 ml) and water (20 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 by volume)

Sources & evidence

ORD record
ord-89e82c55802f4b0eba1cf34c6bd6dbf6
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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