Triethylamine → HCID 11644115, compound

HRID 645941

Reaction equation

HRID 645941 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH2:11])=[CH:2]1.CCN(CC)CC.[C:19](Cl)(=[O:22])[CH2:20][CH3:21]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH:11][C:19](=[O:22])[CH2:20][CH3:21])=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 4721071H-Indol-3-Ylmethanamine

Product 1

HCID 11644115HCID 11644115, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound 25 (1.00 g, 6.84 mmol) and Et3N (1.4 mL, 10.26 mmol) were dissolved in MeOH and cooled to 0° C. Propionyl chloride (633 mg, 6.84 mmol) was added dropwise and the reaction was stirred at room temperature for 4 hours. The volatiles were removed and the residue was taken up in CH2Cl2 (40 mL), washed with 10% citric acid (20 mL), satd. NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried with Na2SO4, filtered and the volatiles were removed to yield 1.33 g of a white, crystalline solid (1.33 g, 96% yield). An analytical sample was recrystallized from EtOAc/hexanes. m.p.=91-92° C. 1H NMR (CDCl3) δ 8.80 (br s, 1H, NH), 7.62 (d, 1H, ArH, J=7.85 Hz), 7.38 (d, 1H, ArH, J=7.2 Hz), 7.20 (3H, ArH), 5.80 (br s, 1H, NH), 4.60 (d, 2H, ArCH2, J=5.1 Hz), 2.20 (q, 2H, COCH2CH3, J=7.6 Hz), 1.14 (t, 3H, COCH2CH3, J=7.6 Hz). 13C NMR (CDCl3) δ 173.6, 136.5, 126.6, 123.3, 122.5, 119.9, 118.8, 112.8, 111.4, 35.2, 29.7, 9.9. IR (KBr) vmax cm−1: 3405, 1891, 1634, 1532, 1097.

Workup

  1. customThe volatiles were removed
  2. washwashed with 10% citric acid (20 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customthe volatiles were removed

Sources & evidence

ORD record
ord-b2988a1a55f94c6da54b2f568f2f9a0e
Source dataset
uspto-grants-2010_04
Patent number
US07705022B2

Linked notes

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