4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 22111000, compound

HRID 565627Notes

Reaction equation

HRID 565627 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]2[O:4][C:3]([CH2:2][N:27]3[CH2:26][CH2:25][C:24]([C:21]4[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=4)([OH:30])[CH2:29][CH2:28]3)([CH3:16])[CH2:7][C:6]=2[C:8]=1[CH3:15]

Participants

4

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidine2×HCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 22111000HCID 22111000, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g) and 4-(4-chlorophenyl)-4-hydroxypiperidine (1.3 g) in xylene (10 mL) was stirred under nitrogen gas at 120° C. for 1.5 hours and, then, refluxed for 16 hours. Thereafter, 0.85 g of 4-(4-chlorophenyl)-4-hydroxypiperidine was added and the mixture was refluxed for 24 hours. After cooling, the reaction mixture was filtered and washed with diethyl ether. The filtrate was extracted with 1N-hydrochloric acid and the aqueous layer was made weakly acidic with saturated aqueous sodium hydrogen carbonate (NaHCO3). This aqueous layer was washed with diethyl ether and made weakly basic with saturated aqueous NaHCO3. This solution was extracted with ethyl acetate and the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from diethyl ether/hexane to provide 0.58 g of the title compound. Yield 28%.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperaturethe mixture was refluxed for 24 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. washwashed with diethyl ether
  6. extractionThe filtrate was extracted with 1N-hydrochloric acid
  7. washThis aqueous layer was washed with diethyl ether
  8. extractionThis solution was extracted with ethyl acetate
  9. washthe organic layer was washed with saturated aqueous NaCl
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-31b685027ca344138521e2170951eebf
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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