Methanol → HCID 86730079, compound

HRID 880020Notes

Reaction equation

HRID 880020 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:14]1.C(N(CC)CC)C.CO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86730079HCID 86730079, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorobenzene-1-sulfonyl chloride (470 mg, 1.91 mmol) was added tert-butyl piperidin-4-ylmethylcarbamate (410 mg, 1.91 mmol) followed by triethylamine (0.267 mL, 1.91 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with DCM and the organic portion washed with 1N HCl, H2O, and brine, dried over Na2SO4 and decanted. The solvent was evaporated under reduced pressure and the crude residue was purified by flash chromatography on a 24 g silica gel cartridge using 0 to 100% ethyl acetate in hexane over 15 minutes, then 0 to 20% MeOH in DCM over 15 min. to provide Intermediate 3A (800 mg, 1.890 mmol, 99% yield). HPLC/MS (Method M) RT=1.58 min, [M+1]+ 324.1.

Workup

  1. washthe organic portion washed with 1N HCl, H2O, and brine
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. customThe solvent was evaporated under reduced pressure
  5. customthe crude residue was purified by flash chromatography on a 24 g silica gel cartridge
  6. customover 15 minutes

Sources & evidence

ORD record
ord-82a3f7b0b7e64f32ad1d9a89776ddef9
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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