Hydrochloric Acid → 2-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile

HRID 896254Notes

Reaction equation

HRID 896254 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>C1COCC1.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 223496205-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrile

Product 1

HCID 223496642-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrileYield 75.5%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2-nitro-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile (1.1 g, 3.6 mmol) in THF (20 ml) in presence of benzyltrimethylammonium chloride (334 mg, 1.8 mmol) was treated by a slow addition of Na2S2O4 (3.1 g, 18 mmol) in water (20 ml). After 0.5 h, HCl (6N, 20 ml) was added to the mixture, which was stirred at 60° C. for 5 h. The mixture was cooled to room temperature, extracted with ethylacetate. The aqueous phase was made basic with Na2 CO3 (solid), and extracted with ethylacetate. The organic phase was dried over MgSO4, concentrated, to give a yellow solid (748 mg, 75%) of title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-274159f323c348ee8e4688369550225b
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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