Formaldehyde → tert-Butyl 4-[2-(methylamino)ethyl]piperidine-1-carboxylate

HRID 1480434Notes

Reaction equation

HRID 1480434 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:19][NH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46835695tert-Butyl 4-[2-(methylamino)ethyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (1.0 g, 4.38 mmol) was dissolved in DCM (40 ml) and treated with 36.5% formaldehyde solution (326 μl, 4.38 mmol) followed by acetic acid (1 drop). The reaction mixture was stirred for 20 mins and treated with sodium triacetoxyborohydride (93 mg, 0.438 mmol). The resulting mixture was stirred at ambient temperature for 16 hrs and quenched with 2M NaOH (40 ml). The mixture was extracted with DCM (2×100 ml) and the combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to give tert-butyl 4-(2-(methylamino)ethyl)piperidine-1-carboxylate as an oil;

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 16 hrs
  2. customquenched with 2M NaOH (40 ml)
  3. extractionThe mixture was extracted with DCM (2×100 ml)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e445386113dd44bb933994f9f910d2da
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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