Tetrahydrofuran → 4-(1H-Imidazol-1-yl)phenyl-4-methyl-1-piperidine ethanol

HRID 232335

Reaction equation

HRID 232335 reaction equation
Br[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1)O.[CH3:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[O:23]1CCCC1>>[N:11]1([C:8]2[CH:9]=[CH:10][C:5]([CH:3]3[CH2:2][CH:17]([CH3:16])[CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][OH:23])=[CH:6][CH:7]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 693814-MethylpiperidineHCID 20031362alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

Product 1

HCID 178455204-(1H-Imidazol-1-yl)phenyl-4-methyl-1-piperidine ethanol

Procedure

Add α-(bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol (8.88 g, 33.24 mmol) to a room temperature solution of 4-methylpiperidine (11.8 mL, 99.73 mmol) in tetrahydrofuran (90mL). Stir the resultant mixture for 2.5 days and concentrate in vacuo. Chromatograph the residue on alumina (neutral, activity III, 100 g) using first methylene chloride than 2% methanol in methylene chloride as eluent. Collect the product fraction and concentrate in vacuo to give a solid. Recrystallize the solid from petroleum ether/ethyl acetate (ca. 4+1). Drying at 50° C. for 2 hr at p=1.0 mm affords the title compound.

Workup

  1. concentrationconcentrate in vacuo
  2. customCollect the product fraction
  3. concentrationconcentrate in vacuo
  4. customto give a solid
  5. customRecrystallize the solid from petroleum ether/ethyl acetate (ca. 4+1)
  6. customDrying at 50° C. for 2 hr at p=1.0 mm

Sources & evidence

ORD record
ord-5c272afe37204cc6941c112a84e35e56
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

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