Triethylamine → HCID 3802318, compound

HRID 1291151Notes

Reaction equation

HRID 1291151 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br.C(N(CC)CC)C>CN(C)C=O>[F:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680073-Fluorobenzyl bromideHCID 79341Piperidin-4-ol

Product 1

HCID 3802318HCID 3802318, compoundYield 44.8%

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 3-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. 1.19 g (36%) of 1-(3-fluoro-benzyl)-piperidin-4-ol was obtained as yellow crystals; m.p. 61°-62°.

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-79a5026af527465eb25f426f558e0cf3
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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