N-Methylethylamine → HCID 68576156, compound

HRID 273085Notes

Reaction equation

HRID 273085 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[CH2:20]([NH:22][CH3:23])[CH3:21]>C(#N)C.[I-].[K+]>[CH2:20]([N:22]([CH3:23])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH3:21]

Participants

5

Reactant 2

HCID 12219N-MethylethylamineHCID 68576473HCID 68576473, compound

Product 1

HCID 68576156HCID 68576156, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-[4-(3-chloro-propoxy)-phenyl]-tetrahydropyran-4-carbonitrile (3.0 g, 10.7 mmol), potassium iodide (100 mg, 0.60 mmol) and ethylmethylamine (5.0 ml, 58.3 mmol) in acetonitrile (30 mL) was heated to 60° C. overnight. The mixture was cooled, concentrated in vacuo and partitioned between dilute Na2CO3 solution (40 ml) and ethyl acetate (80 ml). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude material was carried out with flash chromatography (silica gel, ethyl acetate/methanol/aqueous ammonia 98:2:0.2 to 85:15:1.5) to afford 4-(4-{3-[ethyl(methyl)amino]propoxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile as a pale yellow oil (2.0 g, 6.6 mmol, 62%). 1H NMR (400 MHz CDCl3) δ 1.06 (t, 3H), 1.91-2.00 (m, 2H), 2.00-2.14 (m, 4H), 2.25 (s, 3H), 2.40-2.50 (m, 2H), 2.53 (t, 2H), 3.89 (m, 2H), 4.00-4.11 (m, 4H), 6.91 (d, 2H), 7.38 (d, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. custompartitioned between dilute Na2CO3 solution (40 ml) and ethyl acetate (80 ml)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude material

Sources & evidence

ORD record
ord-ea39d3115ac846faaf00a45e95b1a25e
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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