Hydrochloric Acid → HCID 19841142, compound

HRID 1638660Notes

Reaction equation

HRID 1638660 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[C:4](F)[C:3]=1[CH3:13].O.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.Cl>C(O)C.C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[C:4]([N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[C:3]=1[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 531671-MethylpiperazineHCID 14834653HCID 14834653, compound

Product 1

HCID 19841142HCID 19841142, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To 2-chloro-5,6-difluoro-3-nitrotoluene (54 mg) are added ethanol (0.3 ml) and water (0.03 ml) at 0° C. and thereto further added dropwise a solution of N-methylpiperazine (0.04 ml) and triethylamine (0.06 ml) in ethanol (0.1 ml) at room temperature. The mixture is stirred at room temperature for 5 hours, at 60° C. for 5 hours and further at 80° C. overnight. The reaction mixture is acidified with 2N hydrochloric acid and washed with a small amount of diethyl ether and then neutralized with aqueous saturated sodium hydrogen carbonate and extracted with dichloromethane. The extract is washed with water and aqueous saturated sodium chloride in this order and dried over anhydrous magnesium sulfate, and then dichloromethane is disilled off to give 2-chloro-5-fluoro-6-(4-methyl-1-piperazinyl)-3-nitrotoluene (35 mg).

Workup

  1. washwashed with a small amount of diethyl ether
  2. extractionextracted with dichloromethane
  3. washThe extract is washed with water and aqueous saturated sodium chloride in this order
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-04e4437dfdc64ad6b3164411aa386974
Source dataset
uspto-grants-1989_11
Patent number
US04880806

Reaction notes

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