Triethylamine → HCID 21080296, compound

HRID 346676Notes

Reaction equation

HRID 346676 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.Cl.Cl[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 21080296HCID 21080296, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

A stirred mixture of 4-(4-fluorobenzoyl)piperidine, hydrochloride salt (3.90 g), 4-chloropyridine, hydrochloride salt (2.85 g) and triethylamine (4.90 ml) in xylene (75 ml) was heated at 145° C. for 27 hours. The solvent was evaporated and the residue partitioned between methylene chloride (150 ml) and water (100 ml), the pH being adjusted to ˜10 with 0.880 ammonia. The aqueous phase was extracted with a further methylene chloride (50 ml). The combined organic phases were washed with water, dried (Mg SO4) and evaporated. The residue was purified by column chromatography using a 19:1 mixture of methylene chloride and methanol as eluent to give 4-(4-fluorobenzoyl)-1-(4-pyridyl)piperidine (1.89 g);

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between methylene chloride (150 ml) and water (100 ml)
  3. extractionThe aqueous phase was extracted with a further methylene chloride (50 ml)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (Mg SO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. additiona 19:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-ac4f1fa9ce0646a0b3a103b3ba3484c7
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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