Picolyl chloride → HCID 53784609, compound

HRID 1292356Notes

Reaction equation

HRID 1292356 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:21][CH:20]1[C:32]([NH2:34])=[O:33])=[O:18].[CH:35](N(C(C)C)CC)(C)C.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1CCl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:35][C:48]3[CH:49]=[N:44][CH:45]=[CH:46][CH:47]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][C:4]=1[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH2:21][CH:20]1[C:32]([NH2:34])=[O:33])=[O:18]

Participants

5

Reactant 3

HCID 23393Picolyl chloride2×HCID 81531Diisopropylethylamine2×HCID 54376204HCID 54376204, compound

Product 1

HCID 53784609HCID 53784609, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Methoxy-4-(4-piperidyloxy)phenylacetyl)-4-(2-methylphenyl) piperazine-2-carboxamide (110 mg, 0.236 mmole) was dissolved in 3 ml of dry N,N-dimethylformamide. To this solution was added 86 μL (0.496 mmole) of diisopropylethylamine (DIEA) and 43 mg (0.26 mmole) of picolyl chloride. The reaction mixture was stirred at ambient temperature overnight and then was treated with an additional 20 mg of picolyl chloride. The pH of the reaction mixture was adjusted to 9 with DIEA and stirring was continued for 24 hr more. All volatiles were removed under reduced pressure and the residual material was partitioned between ethyl acetate and water. The organic phase was washed with 5% sodium carbonate solution and brine, then dried and concentrated. The crude product mixture was purified via preparative thick layer chromatography on precoated silica gel plates (80:20 chloroform-methanol elution) to give the title compound in homogeneous form: m.p. 78°-81° C.

Workup

  1. stirringstirring
  2. waitwas continued for 24 hr
  3. customAll volatiles were removed under reduced pressure
  4. customthe residual material was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 5% sodium carbonate solution and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product mixture was purified via preparative thick layer chromatography on precoated silica gel plates (80:20 chloroform-methanol elution)

Sources & evidence

ORD record
ord-789408ba28fe4ab386459fab05c27590
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Reaction notes

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