HCID 22494716, compound → HCID 58107469, compound

HRID 1810186Notes

Reaction equation

HRID 1810186 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[Cl:25][C:26]1[CH:37]=[CH:36][C:29]([C:30](N(OC)C)=[O:31])=[CH:28][C:27]=1[S:38](=[O:41])(=[O:40])[NH2:39]>O1CCCC1>[Cl:25][C:26]1[CH:37]=[CH:36][C:29]([C:30](=[O:31])[C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)=[CH:28][C:27]=1[S:38]([NH2:39])(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 22494716HCID 22494716, compoundHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 58107469HCID 58107469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.227 g of 1-(4-bromo-phenyl)-4-phenyl-piperidine in tetrahydrofuran (5 mL) is cooled to −78° C. and treated with 2 portions of 0.29 mL each of tert-butyllithium (1.5 M in pentane). After 20 min at −78° C. the reaction mixture is treated with 0.1 g of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (5 mL) and stirred for another 1.5 h. The temperature is then increased slowly to 0° C. and after completion the reaction is quenched by addition of 2 mL of saturated aqueous ammonium chloride and extracted with diethyl ether. The organics are washed with water, dried over magnesium sulfate, concentrated to 0.27 g of crude product which is purified by silica gel chromatography (1:1 hexanes/ethyl acetate) to give 2-chloro-5-[4-(4-phenyl-piperidin-1-yl)-benzoyl]-benzenesulfonamide as a powder. MS (m/z): (M−1) 453; Rf 0.65 (1:1 hexanes/ethyl acetate)

Workup

  1. customafter completion the reaction is quenched by addition of 2 mL of saturated aqueous ammonium chloride
  2. extractionextracted with diethyl ether
  3. washThe organics are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to 0.27 g of crude product which
  6. customis purified by silica gel chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-062e26932b8c48628ee02650a688cf30
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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