N-methoxy-N-methylcycloheptanecarboxamide → Cycloheptyl(3-pyridinyl)methanone

HRID 900762Notes

Reaction equation

HRID 900762 reaction equation
CON(C)[C:4]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[Li][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>CCOCC>[CH:6]1([C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 12094213N-methoxy-N-methylcycloheptanecarboxamideHCID 178418470HCID 178418470, compound

Product 1

HCID 65399931Cycloheptyl(3-pyridinyl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%).

Workup

  1. customquenched by addition of aqueous saturated NH4Cl
  2. temperatureto warm to room temperature
  3. additiondiluted with ether
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted 3 times with ether
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customAfter purification by chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-0f24c4cbb8bd417592cd9710636e0e75
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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