Triethylamine → HCID 9864520, compound

HRID 2392578Notes

Reaction equation

HRID 2392578 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:21]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 18980215HCID 18980215, compound

Product 1

HCID 9864520HCID 9864520, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-(6-fluorobenzo[b]thien-3-yl)-1-piperazine-butanamine (4.04 g, 13.1 mmol), triethylamine (1.89 g, 18.6 mmol), and dichloromethane (50 mL) under a nitrogen atmosphere was added isobutyryl chloride (1.63 g, 15.3 mmol) over 6 minutes. The reaction was stirred at 0° C. for 4 hours and then was diluted with dichloromethane (140 mL). The mixture was washed successively with 5% aqueous NaOH (100 mL) and water (100 mL), dried (K2CO3), and concentrated in vacuo to give an off-white solid. The crude product was chromatographed on silica gel with 10% methanol/dichloromethane as eluent to afford an off-white solid. Recrystallization from ethyl acetate/heptane gave 2.17 g (43%) of the title compound as beige needles: m.p. 130°-131° C. TLC (silica gel, 10% methanol/dichloromethane) Rf =0.37. The IR(CHCl3), 1H NMR (CDCl3, 200 MHz), and MS (M+ 377, EI, 70 eV) were consistent for the assigned structure.

Workup

  1. washThe mixture was washed successively with 5% aqueous NaOH (100 mL) and water (100 mL)
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated in vacuo
  4. customto give an off-white solid
  5. customThe crude product was chromatographed on silica gel with 10% methanol/dichloromethane as eluent
  6. customto afford an off-white solid
  7. customRecrystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-8e58da1ab95c46cda86c70613f33fe06
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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