Triethylamine → HCID 765229, compound

HRID 1291154Notes

Reaction equation

HRID 1291154 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][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.C(N(CC)CC)C>CN(C)C=O>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 680214-Fluorobenzyl bromideHCID 79341Piperidin-4-ol

Product 1

HCID 765229HCID 765229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.856 g (0.00846 mol) of 4-hydroxypiperidine was dissolved in 40 ml of dimethylformamide and cooled to 0°. 2.0 g (0.0106 mol) of 4-fluorobenzyl bromide and 3.3 ml (0.0233 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 (17:3) as the eluent. An analytically pure sample was obtained after a second chromatography on silica gel with dichloromethane/methanol (17:3) as the eluent. The remainder was used directly in the next step. 0.176 g (8%) of 1-(4-fluoro-benzyl-piperidin-4-ol was 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 (17:3) as the eluent
  6. customAn analytically pure sample was obtained after a second chromatography on silica gel with dichloromethane/methanol (17:3) as the eluent

Sources & evidence

ORD record
ord-c1867705e6ca4e52acb6e55ed59d3aaa
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…