N,N-Dimethylglycine → 1-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidino]-2-(dimethylamino)-1-ethanone

HRID 748806Notes

Reaction equation

HRID 748806 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:26][N:27]([CH3:32])[CH2:28][C:29](O)=[O:30].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>ClCCl.C(OC(C)C)(C)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][N:15]([C:29](=[O:30])[CH2:28][N:27]([CH3:32])[CH3:26])[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 673N,N-DimethylglycineHCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 692029464-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine Hydrochloride

Product 1

HCID 597508661-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidino]-2-(dimethylamino)-1-ethanoneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine hydrochloride (100 mg, 0.245 mmol) obtained in Example 260, N,N-dimethylglycine (40 mg, 0.39 mmol) and N-methylmorpholine (0.142 ml, 1.29 mmol) were dissolved in dichloromethane (5 ml), followed by the addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (80 mg, 0.42 mmol) at room temperature. After stirring at room temperature for 14 hours, a saturated aqueous solution (0.5 ml) of sodium bicarbonate was added. The residue obtained by concentrating the reaction mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the dichloromethane:methanol=30:1 eluate was concentrated under reduced pressure to give a white solid. The resulting solid was washed with diisopropyl ether, whereby the title compound (70 mg, 0.15 mmol, 62%) was obtained as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customthe fraction obtained from the dichloromethane
  4. concentrationmethanol=30:1 eluate was concentrated under reduced pressure
  5. customto give a white solid

Sources & evidence

ORD record
ord-f44f9405391c42c594c0be2b9d1b5c1c
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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