Triethylamine → HCID 765448, compound

HRID 1291162Notes

Reaction equation

HRID 1291162 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Br)([O-:10])=[O:9].C(N(CC)CC)C>CN(C)C=O>[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 79341Piperidin-4-ol

Product 1

HCID 765448HCID 765448, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.41 g (0.01389 mol) of 4-hydroxypiperidine were dissolved in 60 ml of dimethylformamide and cooled to 0°. 3.0 g (0.01389 mol) of 3-nitrobenzyl bromide and 4.3 ml (0.03056 mol) of triethylamine were added under argon and the mixture was left to come to room temperature. It was stirred for 16 hrs., the solvent was distilled off and the residue was taken up in dichloromethane. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated and the residue was chromatographed on silica gel with dichloromethane/methanol (19:1) as the eluent. 1.9 g (58%) of 1-(3-nitro-benzyl)-piperidin-4-ol were obtained as a yellow oil. MS: me/e=237 (C12H17N2O3+)

Workup

  1. temperaturecooled to 0°
  2. waitthe mixture was left
  3. customto come to room temperature
  4. distillation, the solvent was distilled off
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue was chromatographed on silica gel with dichloromethane/methanol (19:1) as the eluent

Sources & evidence

ORD record
ord-1ba0eaf07b644a3ebed16a47dd5df114
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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