Dichloromethane → HCID 69459970, compound

HRID 458949Notes

Reaction equation

HRID 458949 reaction equation
C1(C(O)CCN2CCCC[CH:11]2[N:16]([CH2:30][CH3:31])[C:17](=[O:29])[CH2:18][C:19]2[CH:24]=[CH:23][C:22](S(C)(=O)=O)=[CH:21][CH:20]=2)C=CC=CC=1.[CH2:33]([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])[CH3:34].[CH3:40][S:41](Cl)(=[O:43])=[O:42].[CH2:45]([Cl:47])Cl>>[C:19]1([CH:45]([Cl:47])[CH2:34][CH2:33][N:35]2[CH2:38][CH2:39][CH:11]([N:16]([CH2:30][CH3:31])[C:17](=[O:29])[CH:18]([S:41]([CH3:40])(=[O:43])=[O:42])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:37][CH2:36]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69462239HCID 69462239, compound

Product 1

HCID 69459970HCID 69459970, compoundYield 44%

Procedure

To a mixture of N-[1-(3-phenyl-3-hydroxypropyl)-piperidinyl]-N-ethyl-4-methanesulfonylphenylacetamide (400 mg, 0.87 mmol) and triethylamine (0.24 mL, 1.04 mmol) in DCM (10 mL) at 0° C. was added methane sulfonyl chloride (67 μL, 0.87 mmol). The resulting mixture was stirred at room temperature for 30 min. then evaporated. The residue was purified by eluting through a 20 g Bond Elut to give the title compound (180 mg, 44%); NMR (CDCl3): 1.1 (t, 1H), 1.2 (m, 2H), 1.6 (m, 7H), 2.2 (m, 2H), 2.4 (m, 2H), 2.8 (m, 2H), 3.0 (s, 3H), 3.3 (m, 2H), 3.8 (m, 2H), 5.0 (m, 1H), 7.3 (m, 5H), 7.4 (d, 2H), 7.9 (d, 2H); MS: 477.

Workup

  1. customthen evaporated
  2. customThe residue was purified
  3. washby eluting through a 20 g Bond Elut

Sources & evidence

ORD record
ord-e53b75d7d2e345f5ac73a32a338cfa6e
Source dataset
uspto-grants-2007_03
Patent number
US07192973B2

Reaction notes

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