4-chloro-N-methylpiperidine → HCID 14637760, compound

HRID 1534584Notes

Reaction equation

HRID 1534584 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5](Cl)[CH2:4][CH2:3]1.[CH3:9][O:10][C:11]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[C:14]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:13]=2[CH:12]=1>C1COCC1>[CH3:9][O:10][C:11]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)([OH:22])[C:14]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 793424-chloro-N-methylpiperidineHCID 143698038-Chloro-5-methoxy-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

Product 1

HCID 14637760HCID 14637760, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a 1.5 M Grignard solution of N-methyl 4-chloropiperidine (150 mL, 22.5 mmol) in THF dropwise over a 7 minute period to 5-methoxy-8-chloro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (5.00 g, 18.4 mmol) in THF (70 mL) at 0° C. and under an argon atmosphere. Quench the reaction after 30 minutes with a saturated solution of NH4Cl (pH 8) and extract (3×) with CHCl3. Combine the organic portions, wash with brine, dry over sodium sulfate, filter and concentrate in vacuo. Purify via flash chromatography (CH3OH 5% in CH2Cl2) to give the title compound (3.60 g, 53%) as a solid. The solid may be recrystallized from isopropyl ether to give a white powder (mp 168°-170° C.).

Workup

  1. customQuench
  2. customthe reaction after 30 minutes with a saturated solution of NH4Cl (pH 8)
  3. extractionextract (3×) with CHCl3
  4. washwash with brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify via flash chromatography (CH3OH 5% in CH2Cl2)

Sources & evidence

ORD record
ord-77bc1a9185ae4542a50b28e3a92ee454
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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