Dichloromethane → HCID 60926797, compound

HRID 2200184Notes

Reaction equation

HRID 2200184 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C.C(Cl)Cl>CS(C)=O.CO>[CH3:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 612132-Chloro-5-nitrobenzotrifluorideHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 60926797HCID 60926797, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Dissolve 1-chloro-4-nitro-2-(trifluoromethyl)benzene (1.0 g, 4.44 mmol) in DMSO (5 mL), add 1-methylpiperidin-4-amine (0.56 g, 4.89 mmol) and DIEA (1.72 g, 13.3 mmol) and stir the reaction at 80° C. overnight. TLC (DCM:MeOH=10:1) shows the reaction is complete. Add water, extract with EtOAc (10 mL×3), combine the organic layers, wash with water and brine sequentially, and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the crude product. Purification by chromatography (silica gel, MeOH:DCM=1:15) affords the title compound (587 mg, 44%). MS: (M+1): 304.2.

Workup

  1. customthe reaction at 80° C. overnight
  2. extractionAdd water, extract with EtOAc (10 mL×3)
  3. washwash with water and brine sequentially
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure
  6. customto get the crude product
  7. customPurification by chromatography (silica gel, MeOH:DCM=1:15)

Sources & evidence

ORD record
ord-94f021d706d241fe9d8e28b1a904655f
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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