Dimethylformamide → HCID 765041, compound

HRID 1291167Notes

Reaction equation

HRID 1291167 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.CN(C)[CH:21]=[O:22]>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:14]2[CH2:15][CH2:16][CH:21]([OH:22])[CH2:18][CH2:17]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 765041HCID 765041, compound

Procedure

1.0 g (0.00989 mol) of 4-hydroxypiperidi,ne was dissolved in 50 ml of dimethylformamide and cooled to 0°. 2.56g (0.001186 mol) of 4-nitro-benzyl bromide and 2.78 ml (0.0198 mol) of triethylamine were added 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 (9:1) as the eluent. 0.836 g (36%) of 1-(4-nitro-benzyl-piperidin-4-ol was obtained as beige crystals; m.p. 114°-115°.

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 (9:1) as the eluent

Sources & evidence

ORD record
ord-6f2fe62fa2a94975b3b7cdb543531a8a
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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