Hexane → HCID 67364898, compound

HRID 1182725Notes

Reaction equation

HRID 1182725 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:10])[CH3:9].C([Li])CCC.CCCCCC.[CH2:22]([N:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.CCOCC.O>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]([OH:10])[CH3:9])([OH:35])[CH2:31][CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 192201-Benzyl-4-piperidoneHCID 954551-(2-Bromophenyl)ethanolHCID 178418339Butyllithium

Product 1

HCID 67364898HCID 67364898, compoundYield 49.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (RS)-1-(2-bromo-phenyl)-ethanol (8.0 g, 39.8 mmol) −70° C. in tetrahydrofuran (40 ml) was added dropwise a 1.6M n-butyllithium solution in hexane (57.2 ml, 91.5 mmol) over a period of 20 min. After 2 hours, a solution of 1-benzyl-4-piperidone (10.2 ml, 55.7 mmol) in tetrahydrofuran (32 ml) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was poured into a stirred mixture of water (200 ml) and ether (200 ml). The aqueous layer was extracted with ether (2×100 ml). The combined extracts were washed with water (80 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel (eluent: heptane/ethylacetate 3:7) to yield 6.1 g (49%) of (RS)-1-benzyl-4-[2-(1-hydroxy-ethyl)-phenyl]-piperidin-4-ol as a white solid. MS m/e: 312 (M+H+).

Workup

  1. extractionThe aqueous layer was extracted with ether (2×100 ml)
  2. washThe combined extracts were washed with water (80 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was chromatographed on silica gel (eluent: heptane/ethylacetate 3:7)

Sources & evidence

ORD record
ord-ecb2806686c24b9db47d518d6eb30322
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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