Acetic Acid → 4-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine

HRID 1946897Notes

Reaction equation

HRID 1946897 reaction equation
[CH:1]([O:4][C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[CH:7][C:8]([CH3:18])=[C:9]([C:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2].[CH3:22][NH:23][CH3:24].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO>[CH:1]([O:4][C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[CH:7][C:8]([CH3:18])=[C:9]([C:11]2[CH2:16][CH2:15][CH:14]([N:23]([CH3:24])[CH3:22])[CH2:13][CH:12]=2)[CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 597643864-(5-Isopropoxy-2-methyl-4-nitrophenyl)cyclohex-3-enone

Product 1

HCID 597644704-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4-(5-isopropoxy-2-methyl-4-nitrophenyl)cyclohex-3-enone (0.1 mmol) and dimethylamine (0.11 mmol) in 2 mL of 1,2-dicholoroethane, is added AcOH (0.1 mmol) and NaBH(OAc)3 (0.11 mmol). The reaction mixture is stirred at room temperature for 10 hours. After workup and silica flash chromatography (CH2Cl2/MeOH 9:1), 4-(5-isopropoxy-2-methyl-4-nitrophenyl)-N,N-dimethylcyclohex-3-enamine is obtained. MS (ES+): 319.19 (M+1)+.

Sources & evidence

ORD record
ord-990b001d66c54bf1846f1d18727d6726
Source dataset
uspto-grants-2013_03
Patent number
US08399450B2

Reaction notes

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