Sodium Carbonate → 1-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-[5-(4-chlorophenyl)-2-thiophenesulfonyl]-2-piperazinone

HRID 2186162Notes

Reaction equation

HRID 2186162 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:12](=[O:30])[CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([S:7]([C:5]3[S:6][C:2]([C:35]4[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=4)=[CH:3][CH:4]=3)(=[O:9])=[O:8])[CH2:11][C:12]2=[O:30])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 234475704-(5-Bromo-2-thiophenesulfonyl)-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

Product 1

HCID 234476131-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-[5-(4-chlorophenyl)-2-thiophenesulfonyl]-2-piperazinoneYield 92.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-(5-bromo-2-thiophenesulfonyl)-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone (115 mg), 4-chlorophenylboronic acid (52 mg), tetrakistriphenylphosphine palladium (25 mg), 2M sodium carbonate solution (0.25 ml) and dimethoxyethane (10 ml) was refluxed for 15 hours. The reaction solution was concentrated, and to the residue was sodium bicarbonate solution. The mixture was extracted with ethyl acetate, washed with brine, dried, and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:3) to give colorless solid of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-[5-(4-chlorophenyl)-2-thiophenesulfonyl]-2-piperazinone (113 mg).

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationThe reaction solution was concentrated
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-595c72d95b7344c7a0c59cf417f5fd75
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

Loading…