Acetic Acid → 2-(2-amino-5-(piperidin-1-yl)phenyl)-N-(3,4-dimethylphenyl)pyridin-4-amine

HRID 1408137Notes

Reaction equation

HRID 1408137 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:21]=[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH:19]=[CH:18][C:17]=3[N+:28]([O-])=O)[CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(O)(=O)C>O1CCCC1.CCO.[Zn]>[NH2:28][C:17]1[CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:21][C:16]=1[C:12]1[CH:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66586790N-(3,4-dimethylphenyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridin-4-amine

Product 1

HCID 665869052-(2-amino-5-(piperidin-1-yl)phenyl)-N-(3,4-dimethylphenyl)pyridin-4-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Into a 50-mL 3-necked round bottom flask, was placed a solution of N-(3,4-dimethylphenyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridin-4-amine (300 mg, 0.75 mmol, 1.00 equiv) in tetrahydrofuran/EtOH (10/1 mL), Zn (485 mg, 7.46 mmol, 10.00 equiv), and acetic acid (1 mL). The resulting solution was stirred for 30 min at room temperature. The solids were filtered out. The solution was adjusted to pH 7-8 with sodium bicarbonate (aq). The resulting solution was extracted with 3×25 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 1×25 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The product was obtained as 270 mg (97%) of a yellow solid.

Workup

  1. customInto a 50-mL 3-necked round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. extractionThe resulting solution was extracted with 3×25 mL of dichloromethane
  4. washThe resulting mixture was washed with 1×25 mL of brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-29d9362eb4724a10837a280ff1d04a19
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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