Pyridine → 4-[(3-Chloro-4-fluoro-benzenesulfonylamino)-methyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2180172Notes

Reaction equation

HRID 2180172 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:21][NH2:22])([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:25]=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[CH:28][C:29]=1[F:30].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:21][NH:22][S:31]([C:26]2[CH:27]=[CH:28][C:29]([F:30])=[C:24]([Cl:23])[CH:25]=2)(=[O:33])=[O:32])([C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 207794744-Aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 685333514-[(3-Chloro-4-fluoro-benzenesulfonylamino)-methyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl esterYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-aminomethyl-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.10 g, 0.24 mmol) in CH2Cl2 (1.0 mL) at room temperature under Ar was added a solution of 3-chloro-4-fluorophenylsulfonyl chloride (0.06 g, 0.26 mmol, 1.1 eq.) followed by pyridine (0.25 mL). The mixture was stirred at room temperature for 16 h, diluted with EtOAc (5 mL), washed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL) and dried over Na2SO4. Filtration and rotary evaporation yielded the crude 4-[(3-chloro-4-fluoro-benzenesulfonylamino)-methyl]-4-(4-iodo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (0.09 g, 0.14 mmol, ˜62%). 1HNMR (300 MHz, CDCl3): δ 8.66 (d, 1H), 7.81-7.73 (m, 3H), 7.34 (m, 1H), 7.15 (d, 1H), 7.08 (d, 1H), 3.79 (m, 2H), 3.13 (m, 3H), 2.19 (m, 3H), 1.77 (m, 2H), 1.56 (s, 9H). MS(ESI): 509 (M−Boc).

Workup

  1. washwashed with saturated aqueous NaHCO3 (5 mL) and saturated brine (5 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and rotary evaporation

Sources & evidence

ORD record
ord-a791a2066f8340a28acd5af6dea2513d
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

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