4-Methoxybenzenesulfonyl chloride → HCID 17980045, compound

HRID 348551Notes

Reaction equation

HRID 348551 reaction equation
ClC1C=CC(N(C2CCNCC2)C(=O)C2C=CC=C(OC)C=2)=CC=1.C(OC([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)[CH2:34][CH2:33]1)=O)(C)(C)C.[CH3:46][O:47][C:48]1[CH:53]=[CH:52][C:51]([S:54](Cl)(=[O:56])=[O:55])=[CH:50][CH:49]=1>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[F:45][C:42]1[CH:41]=[CH:40][C:39]([N:38]([CH:35]2[CH2:34][CH2:33][NH:32][CH2:37][CH2:36]2)[S:54]([C:51]2[CH:50]=[CH:49][C:48]([O:47][CH3:46])=[CH:53][CH:52]=2)(=[O:56])=[O:55])=[CH:44][CH:43]=1

Participants

7

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 16413902tert-Butyl 4-(4-fluoroanilino)piperidine-1-carboxylateHCID 17980050HCID 17980050, compound

Product 1

HCID 17980045HCID 17980045, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared as in example 98, steps (A) to (C). Step (B) (acylation) was substituted by the following sulphonylation procedure. To a solution of 4-(4-fluoro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (4.00 g, 13.6 mmol) in dichloromethane (60 ml) and pyridine (32 ml) was added 4-methoxybenzenesulfonyl chloride (3.40 g, 16.3 mmol). After 40 hours stirring at room temperature, the reaction mixture was diluted with ethyl acetate (80 ml), washed with chlorhydric acid (2×50 ml, 0.5 N) and with saturated sodium hydrogencarbonate (50 ml), dried over sodium sulphate, filtered and concentrated in vacuo. The residue was taken in ether to provide a precipitate. Filtration led to 4-[(4-fluoro-phenyl)-(4-methoxy-benzenesulfonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (4.70 g, 74%) as a off white solid, MS (ISP): m/e=465.2 (M+H+).

Workup

  1. washwashed with chlorhydric acid (2×50 ml, 0.5 N) and with saturated sodium hydrogencarbonate (50 ml)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a precipitate
  6. filtrationFiltration

Sources & evidence

ORD record
ord-91e1e199ca114e0fbd6cfa5b326da14d
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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