4-Hydroxybenzyl Alcohol → [4-(2-Piperidin-1-ylethoxy)phenyl]methanol

HRID 612814Notes

Reaction equation

HRID 612814 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>[OH-].[Na+].[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:21]1([CH2:20][CH2:19][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 1140TolueneHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 9816107[4-(2-Piperidin-1-ylethoxy)phenyl]methanolYield 75%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

4-hydroxybenzyl alcohol (6.2 g, 0.0.05 mol) was dissolved in aqueus sodium hydroxide (SN, 30 mL). Toluene (30 mL) was added followed by 1-(2-chloroethyl) piperidine hydrochloride (9.29 g, 0.05 mol) and benzyltriethylammonium bromide (0.3 g). The reaction mixture was heated with vigorous stirring for 1.5 h. The layers were separated, the aqueous layer was extracted with toluene (2×15 mL). Combined organic extracts and organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulfate, and concentrated on a rotary evaporator to give 8.725 g (75%) of alcohol (3a) as a yellowish brown oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with toluene (2×15 mL)
  4. washCombined organic extracts and organic layer was washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-65b1e7d3fc794e8282339830fb07881d
Source dataset
uspto-grants-1999_12
Patent number
US06005102

Reaction notes

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