4-Methylpiperidine-1-carbonyl Chloride → HCID 15308022, compound

HRID 1450450Notes

Reaction equation

HRID 1450450 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[OH:11][C:12]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][C:13]=1[C:14]#[N:15]>CN(C)C1C=CN=CC=1.C1C=CC=CC=1>[C:14]([C:13]1[CH:16]=[C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][C:12]=1[O:11][C:8]([N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1)=[O:9])#[N:15]

Participants

5

Reactant 2

HCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 19976080HCID 19976080, compound

Product 1

HCID 15308022HCID 15308022, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

4-Methyl-1-piperidinecarbonyl chloride (1.18 ml, 8.01 mmol) was added under a nitrogen atmosphere at room temperature to a solution of 2-hydroxy-5-phenoxybenzonitrile (1.53 g, 7.26 mmol) and 4-dimethylaminopyridine (0.976 g, 7.99 mmol) in 50 ml of benzene and the resulting solution refluxed for 1 hour. The reaction mixture was washed with 1N HCl. The benzene layer was separated, dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give 2.57 g of a white crystalline solid. Recrystallization of this solid from diisopropyl ether-hexane gave the title compound as a white crystalline solid (1.59 g, 65%), mp 54°-58° C.

Workup

  1. temperaturethe resulting solution refluxed for 1 hour
  2. washThe reaction mixture was washed with 1N HCl
  3. customThe benzene layer was separated
  4. dry with materialdried (anhydrous MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9ee3f938a22f4c08a2c6b45eb3fa5209
Source dataset
uspto-grants-1997_02
Patent number
US05602151

Reaction notes

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