Triethylamine → HCID 10242192, compound

HRID 1291148Notes

Reaction equation

HRID 1291148 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Br.C(N(CC)CC)C>CN(C)C=O>[F:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67968alpha-Bromo-o-fluorotolueneHCID 79341Piperidin-4-ol

Product 1

HCID 10242192HCID 10242192, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.28 g (0.0127 mol) of 4-hydroxypiperidine were dissolved in 60 ml of dimethylformamide and cooled to 0°. 3.0 g (0.0159 mol) of 2-fluoro-benzyl bromide and 5.0 ml (0.0349 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 chromatographed on silica gel with dichloromethane/methanol (19:1) as the eluent. 1.76 g (53%) of 2-fluoro-benzyl-piperidin-4-ol were obtained as a yellow oil. MS: me/e=210 (C12H17FNO+).

Workup

  1. temperaturecooled to 0°
  2. waitthe mixture was left
  3. customto come to room temperature
  4. distillation, the solvent was distilled off
  5. customthe residue was chromatographed on silica gel with dichloromethane/methanol (19:1) as the eluent

Sources & evidence

ORD record
ord-5f681ea34b024ef0a1fb02e2e88b77b2
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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