Pyridine → HCID 19369246, compound

HRID 849156Notes

Reaction equation

HRID 849156 reaction equation
N1CCCCC1[CH2:7][CH2:8][CH:9]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:17][S:18]([CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][N:22]1[CH2:7][CH2:8][CH:9]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19369278HCID 19369278, compound

Product 1

HCID 19369246HCID 19369246, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Example 296 B) To the hexahydro-7-[2-(2-piperidyl) ethyl]-1H-azepin-2-one product of Example 296 A (2-3 g, 10 mmol) in anhydrous pyridine (8 mL) and CH2Cl2 (4 mL) was added dropwise methanesulfonyl chloride (0.74 mL) in CH2Cl2 (2 mL). The contents were stirred overnight, concentrated in vacuo and partitioned between CH2Cl2 and water. The CH2Cl2 layer was dried over MgSO4 and concentrated in vacuo leaving an oil. The oil was purified by C18 reverse phase chromatography eluding with a CH3CN/H2O (0.05% TFA) gradient to give hexahydro-7-[2-(2-methylsulfonylpiperidyl)ethyl]-1H-azepin-2-one (1.5 g).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between CH2Cl2 and water
  3. dry with materialThe CH2Cl2 layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customleaving an oil
  6. customThe oil was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-9776bd081c454022b97d9f04b980afff
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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