Ammonium Chloride → N-(1-Benzyl-4-methyl-piperidin-4-yl)-benzene-1,2-diamine

HRID 239117Notes

Reaction equation

HRID 239117 reaction equation
[Cl-].[NH4+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)([CH3:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CO.O1CCCC1>[CH2:3]([N:10]1[CH2:11][CH2:12][C:13]([NH:17][C:18]2[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)([CH3:16])[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86686491(1-Benzyl-4-methyl-piperidin-4-yl)-(2-nitro-phenyl)-amine

Product 1

HCID 86686490N-(1-Benzyl-4-methyl-piperidin-4-yl)-benzene-1,2-diamineYield 54.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

168 mg ferrum was added to 160 mL ammonium chloride in 5 mL water. A solution of 244 mg (1-benzyl-4-methyl-piperidin-4-yl)-(2-nitro-phenyl)-amine in 5 mL methanol and 5 mL tetrahydrofuran were added and the mixture was stirred at 70° C. under nitrogen. The mixture was filtered over Celite and water was added to the filtrate. The solution was extracted with ethylacetate. The organic layer was evaporated to yield 121 mg of the desired product.

Workup

  1. filtrationThe mixture was filtered over Celite and water
  2. additionwas added to the filtrate
  3. extractionThe solution was extracted with ethylacetate
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-c67fc25010d84f66a439423a2d8db466
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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