Cyclohexanone → HCID 69475776, compound

HRID 1034953Notes

Reaction equation

HRID 1034953 reaction equation
[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][N:5]1[C:9]([NH2:10])=[CH:8][C:7]([CH3:11])=[N:6]1.[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)(=O)C>[C:13]1([C:8]2[C:7]([CH3:11])=[N:6][N:5]([CH2:4][CH2:3][N:2]([CH3:12])[CH3:1])[C:9]=2[NH2:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 27585011-[2-(Dimethylamino)ethyl]-3-methyl-1H-pyrazol-5-amine

Product 1

HCID 69475776HCID 69475776, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2-dimethylaminoethyl)-5-methyl-2H-pyrazol-3-ylamine (0.998 g, 5.93 mmol) in acetic acid (10 mL) was treated with cyclohexanone (1.23 mL, 11.86 mmol) at ambient temperature for two days. The volatiles were removed and the residue partitioned between dilute sodium hydroxide and ethyl acetate. The organic phase was washed with water, concentrated and the residue purified by flash chromatography on silica gel using 10% methanol in dichloromethane to give a solid (1.10 g, 75%). MS (DCI): m/z 249 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. customthe residue partitioned between dilute sodium hydroxide and ethyl acetate
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel using 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-69060ed61272473aaface8481d058667
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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