2-Chloro-N,N-dimethylethylamine → HCID 59511252, compound

HRID 1157317Notes

Reaction equation

HRID 1157317 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:13]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:12][NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:28][CH2:29][N:30]([CH3:32])[CH3:31]>CN(C=O)C>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][N:11]1[CH:12]=[C:13]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:10]1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 178452251HCID 178452251, compound

Product 1

HCID 59511252HCID 59511252, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To sodium hydride (0.1 g) taken in a dry 100 ml 3-necked round bottom flask cooled to 0° C., dry dimethylformamide (2 ml) was added. To the above mixture, compound tert-butyl 4-(3-phenyl-1H-pyrazol-4-yl)piperazine-1-carboxylate (0.5 g) in DMF (2 ml) was slowly added at 0° C. After 30 min, 2-chloro-N,N-dimethylethylamine (200 mg) in DMF (1 ml) was added to the above mixture. Reaction mixture was allowed to stir at room temperature for overnight, quenched with ice and extracted with ethyl acetate. The organic layer was washed with water (10 ml), brine and dried over sodiumsulphate. The organic layer was filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 6% Ethyl acetate in hexane as eluant afford tert-butyl 4-(1-(2-(dimethylamino)ethyl)-3-phenyl-1H-pyrazol-4-yl)piperazine-1-carboxylate as half white solid.

Workup

  1. customReaction mixture
  2. customquenched with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water (10 ml), brine
  5. dry with materialdried over sodiumsulphate
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-346302af6e4f4b26a32f8032028c4f13
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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