Triethylamine → HCID 66924416, compound

HRID 1364442

Reaction equation

HRID 1364442 reaction equation
Cl.[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:4]=1[C:5]#[N:6].[I:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C>>[I:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:16]2[CH2:17][CH2:18][CH:13]([CH2:12][O:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:3]([F:2])[C:4]=3[C:5]#[N:6])[CH2:14][CH2:15]2)=[O:25])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 669243782-Fluoro-6-(piperidin-4-ylmethoxy)-benzonitrile hydrochloride

Product 1

HCID 66924416HCID 66924416, compoundYield 84%

Procedure

A mixture of 2-fluoro-6-(piperidin-4-ylmethoxy)-benzonitrile hydrochloride (200 mg; 0.7 mmol) (Example 123, Step 3) was stirred at room temperature with 4-iodobenzoyl chloride (187 mg; 0.7 mmol) and triethylamine (0.3 mL; 2.1 mmol) for 16 hours. Reaction was cooled and quenched with dilute HCl and mixture extracted with ethyl acetate (2×20 mL). Combined organics washed with water, saturated sodium bicarbonate, brine and dried over Na2SO4. Crude material was purified by chromatography using 0.5-1% methanol/DCM gradient to afford 2-[1-(4-iodo-benzoyl)-piperidin-4-ylmethoxy]-6-fluoro-benzonitrile as a white solid. (273 mg; 84% yield).

Workup

  1. customReaction
  2. temperaturewas cooled
  3. customquenched with dilute HCl and mixture
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washCombined organics washed with water, saturated sodium bicarbonate, brine
  6. dry with materialdried over Na2SO4
  7. customCrude material was purified by chromatography

Sources & evidence

ORD record
ord-c4c767405ed04b949c30c6b1cbe2c88e
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Linked notes

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