Sodium hydride → HCID 19888468, compound

HRID 654108Notes

Reaction equation

HRID 654108 reaction equation
[C:1]1([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1>CN(C)C=O.O.C(OCC)(=O)C>[F:34][C:31]1[CH:30]=[CH:29][C:28]([N:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][N:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[S:12]([CH3:15])(=[O:14])=[O:13])[CH2:27][CH2:26]2)=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 706829Methanesulfonamide,N-1-naphthalenyl-HCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 19888468HCID 19888468, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A solution of N-(1-naphthyl)methanesulphonamide (6.6 g) in dry N,N-dimethylformamide (20 cc) is added dropwise to a suspension of sodium hydride (0.9 g, 80% suspension in oil) in N,N-dimethylformamide (50 cc). After stirring for 15 minutes, a solution of 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine (7.2 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 110° C. for 2 hours and 30 minutes and is then cooled and poured in a mixture of water (300 cc) and ethyl acetate (500 cc). The organic phase is washed with water, is diluted with dichloromethane (50 cc), is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa) down to 50 cc. The crystals are filtered off and washed with ethyl acetate (3×50 cc) and then with isopropyl ether (2×30 cc) and are dried. After recrystallization, from ethyl acetate (300 cc), N[3-(4-(4-fluorophenyl)- 1-piperazinyl)propyl]-N-(1-naphthyl)methanesulphonamide (4.84 g) is obtained, melting at 170° C.

Workup

  1. temperatureis then cooled
  2. washThe organic phase is washed with water
  3. additionis diluted with dichloromethane (50 cc)
  4. dry with materialis dried over magnesium sulphate
  5. concentrationis concentrated to dryness under reduced pressure (2.7 kPa) down to 50 cc
  6. filtrationThe crystals are filtered off
  7. washwashed with ethyl acetate (3×50 cc)
  8. dry with materialwith isopropyl ether (2×30 cc) and are dried
  9. customAfter recrystallization

Sources & evidence

ORD record
ord-ebbe1cfa7d044279ae14bc981fe540fb
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

Loading…