Formaldehyde → tert-butyl 1-[2-[N-methyl-N-(tetrahydropyran-4-yl)amino]ethyl]-4-piperidinylcarbamate

HRID 1169406Notes

Reaction equation

HRID 1169406 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.[O:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:25][N:1]([CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:6][CH2:5]1)[CH:21]1[CH2:22][CH2:23][O:18][CH2:19][CH2:20]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 235626471,1-Dimethylethyl N-[1-(2-aminoethyl)-4-piperidinyl]carbamate

Product 1

HCID 70023872tert-butyl 1-[2-[N-methyl-N-(tetrahydropyran-4-yl)amino]ethyl]-4-piperidinylcarbamateYield 100.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Into a solution of tert-butyl 1-(2-aminoethyl)-4-piperidinylcarbamate (2.4 g) and tetrahydro-4H-pyran-4-one (0.79 g) in dichloroethane (35 ml) was added at room temperature sodium triacetoxyborohydride (2.19 g), and the resulting mixture was stirred for 2.5 hours. To the reaction mixture were added 37% formalin (0.65 g) and sodium triacetoxyborohydride (2.19 g), and the resulting mixture was stirred for 64 hours. The reaction mixture was mixed with an aqueous solution of sodium bicarbonate and was extracted with chloroform. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. The resulting organic layer was concentrated under reduced pressure to obtain tert-butyl 1-[2-[N-methyl-N-(tetrahydropyran-4-yl)amino]ethyl]-4-piperidinylcarbamate (2.72 g) as a yellow oil.

Workup

  1. stirringthe resulting mixture was stirred for 64 hours
  2. extractionwas extracted with chloroform
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with magnesium sulfate
  5. concentrationThe resulting organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7eb7df666a9442bcaf934fb882ee1383
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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