Formaldehyde → 1-Methyl-4-(4-nitrophenyl)piperidine

HRID 2117638Notes

Reaction equation

HRID 2117638 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:16]=O>C(O)=O>[CH3:16][N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 219595311-Methyl-4-(4-nitrophenyl)piperidine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
110 °C

Procedure

4-(4-Nitrophenyl)piperidine (515 mg) was added to 4 mL 90% formic acid and 1.5 mL formalin added. The solution was stirred and heated at 110° C. for 17 h, evaporated and the solids dissolved in 20 mL water. After basification to pH 14 with 5M sodium hydroxide solution the precipitated solid was extracted into t-butyl methyl ether (3×30 mL). Drying (sodium sulphate) and evaporating gave pure product as pale cream solid. NMR δ 8.15(d,2H), 7.39(d, 2H), 3.00(m,2H), 2.60(m,1H), 2.31(s, 3H), 2.08 (m, 2H), 1.86 (m, 4H).

Workup

  1. additionadded
  2. customevaporated
  3. dissolutionthe solids dissolved in 20 mL water
  4. extractionAfter basification to pH 14 with 5M sodium hydroxide solution the precipitated solid was extracted into t-butyl methyl ether (3×30 mL)
  5. dry with materialDrying (sodium sulphate)
  6. customevaporating
  7. customgave pure product as pale cream solid

Sources & evidence

ORD record
ord-9f6b2245b24545b3be627ac4ba572eb5
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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