Hydrochloric Acid → 1-{3-[4-(4-Fluorobenzoyl)piperidino]propyl}-4-(2-pyridylmethyl) piperazine 2,6-dione hydrochloride

HRID 1461737Notes

Reaction equation

HRID 1461737 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[CH2:13][C:12](=[O:14])[NH:11][C:10](=[O:15])[CH2:9]1.[H-].[Na+].[Cl:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28](=[O:36])[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1.Cl>CN(C)C=O.C(O)C>[ClH:18].[F:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]([CH:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][N:11]3[C:12](=[O:14])[CH2:13][N:8]([CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:9][C:10]3=[O:15])[CH2:23][CH2:24]2)=[O:36])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 12404419[1-(3-Chloropropyl)piperidin-4-yl](4-fluorophenyl)methanoneHCID 148826924-(2-Pyridylmethyl)-2,6-piperazinedione

Product 1

HCID 148826941-{3-[4-(4-Fluorobenzoyl)piperidino]propyl}-4-(2-pyridylmethyl) piperazine 2,6-dione hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 1.86 g of 4-(2-pyridylmethyl)piperazine 2,6-dione in 30 ml of dimethylformamide is added at 20° C. to a suspension of 0.36 g of sodium hydride. The mixture is brought to 60° C. for 30 minutes and 2.7 g of 1-(3-chloropropyl)-4-(4-fluorobenzoyl)piperidine, dissolved in 30 ml of dimethylformamide, are then added, again at 20° C. The mixture is kept stirring at 20° C. for approximately 15 hours and the reaction is completed by bringing to 70° C. for 2 hours. After concentration, the residue is taken up in water and the product is extracted with benzene. The oil obtained is purified by chromatography under pressure on 280 g of b 230-400 mesh silica, eluting with a mixture of dichloromethane and methanol (93.5:6.5 V/V). The base obtained is converted to the hydrochloride in ethanol. The precipitate obtained is then filtered off.

Workup

  1. additionare then added, again at 20° C
  2. waitby bringing to 70° C. for 2 hours
  3. concentrationAfter concentration
  4. extractionthe product is extracted with benzene
  5. customThe oil obtained
  6. customis purified by chromatography under pressure on 280 g of b 230-400 mesh silica
  7. washeluting with a mixture of dichloromethane and methanol (93.5:6.5 V/V)
  8. customThe base obtained
  9. customThe precipitate obtained
  10. filtrationis then filtered off

Sources & evidence

ORD record
ord-f9fc9fc4a1d34e958e3ec71fbbd0d3cc
Source dataset
uspto-grants-1991_12
Patent number
US05077288

Reaction notes

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