Pyridine → HCID 11608128, compound

HRID 478639Notes

Reaction equation

HRID 478639 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:19](=[O:21])[CH3:20])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 698734-Phenylpiperidine

Product 1

HCID 11608128HCID 11608128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Phenylpiperidine (87 mmol) and pyridine (96 mmol) are dissolved in dry CH2Cl2 (100 ml) and acetylchloride (96 mmol) in CH2Cl2 (40 ml) is added dropwise to the stirred solution at 10° C. The reaction is stirred for 1 hour at rt. The mixture is extracted three times with water and the water phase is extracted again with CH2Cl2. The combined organic phases are dried over sodium sulfate and evaporated. A pale brown oil with Rf=0.13 (ethyl acetate/hexane=1:1) is obtained.

Workup

  1. extractionThe mixture is extracted three times with water
  2. extractionthe water phase is extracted again with CH2Cl2
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customevaporated
  5. customA pale brown oil with Rf=0.13 (ethyl acetate/hexane=1:1) is obtained

Sources & evidence

ORD record
ord-ca110666b0384f00a99ffea359f5cb59
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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