Potassium Carbonate → HCID 59837358, compound

HRID 273087Notes

Reaction equation

HRID 273087 reaction equation
[NH2:1][CH2:2][C:3]1([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:19][CH3:20])[CH3:18])=[CH:11][CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:19]([N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][O:13][C:12]1[CH:21]=[CH:22][C:9]([C:3]2([CH2:2][N:1]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[CH:10][CH:11]=1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 68579061HCID 68579061, compound

Product 1

HCID 59837358HCID 59837358, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-{4-[4-(aminomethyl)tetrahydro-2H-pyran-4-yl]phenoxy}-N-ethyl-N-methylpropan-1-amine (500 mg, 1.6 mmol) and bis(2-bromoethyl)ether (345 mg, 1.5 mmol) in anhydrous acetonitrile (50 mL) was added potassium carbonate (450 mg, 3.3 mmol). The mixture was heated to 60° C. overnight then concentrated in vacuo. The crude product was partitioned between dichloromethane (50 ml) and water (50 ml), the aqueous phase was extracted with dichloromethane (25 ml) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude material was carried out with flash chromatography (silica gel, dichloromethane/methanol/aqueous ammonia 100:0:0 to 96:4:0.4) to afford the title compound as a clear colourless oil (315 mg, 0.84 mmol, 52%). 1H NMR (400 MHz CDCl3) δ 1.05 (t, 3H), 1.82-1.93 (m, 2H), 1.92-2.00 (m, 2H), 2.08-2.20 (m, 6H), 2.25 (s, 3H), 2.39 (s, 2H), 2.40-2.50 (q, 2H), 2.50-2.59 (m, 2H), 3.48-3.60 (m, 6H), 3.70-3.80 (m, 2H), 4.00 (t, 2H), 6.86 (d, 2H), 7.20 (d, 2H). LRMS APCI+ m/z 377 [MH]+. HRMS ESI+ m/z 377.2792 [MH]+.−

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was partitioned between dichloromethane (50 ml) and water (50 ml)
  3. extractionthe aqueous phase was extracted with dichloromethane (25 ml)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude material

Sources & evidence

ORD record
ord-9b803f5e041c4ba7ae8353dbc3f27bb7
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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