Acetic Acid → 5-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrile

HRID 896253Notes

Reaction equation

HRID 896253 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:9]([O:20][CH3:21])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].C=O.[C:24](O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO>[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:24])[CH2:18][CH2:19]2)[C:9]([O:20][CH3:21])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 223496252-Nitro-4-(1-piperidin-4-ylmethoxy)5-methoxybenzonitrile

Product 1

HCID 223496205-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrileYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-nitro-4-(1-piperidin-4-ylmethoxy)5-methoxybenzonitrile (771 mg, 2.65 mmol) in CH2Cl2 (8 ml) and MeOH (4 ml) was reacted for 0.5 hour with formaldehyde (13.3 M, 300 μl, 4 mmol), acetic acid (191 mg, 3.18 mmol) and NaBH(OAc)3 (674 mg, 3.18 mmol) slowly added over 15 minutes. The solution was evaporated, the oily residue was taken up in a mixture of Na2CO3 and ethylacetate, extracted with ethylacetate. The organic phase was dried over MgSO4, evaporated to give title compound as a yellow solid (698 mg, 86%).

Workup

  1. additionslowly added over 15 minutes
  2. customThe solution was evaporated
  3. additionthe oily residue was taken up in a mixture of Na2CO3 and ethylacetate
  4. extractionextracted with ethylacetate
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-1823650ebc5347afa4eeed4ebba104ff
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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