Water → HCID 21473647, compound

HRID 2294020Notes

Reaction equation

HRID 2294020 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][O:15][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

Product 1

HCID 21473647HCID 21473647, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.016 g (0.0050 mol) of (1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanol were added to a suspension of 0.20 g (0.0050 mol) of NaH (60% in oil) in 10 ml of tetrahydrofuran and the mixture was stirred at room temperature for 30 minutes Then, 0.60 ml (0.0050 mol) of benzyl bromide was added and the mixture was stirred at room temperature for a further 2 hours. The reaction mixture was subsequently treated with water and extracted with diethyl ether. The organic phase was dried over MgSO4, concentrated and the residue was chromatographed on silica gel with hexane/ethyl acetate 9:1 to 3:1 as the eluent. 0.515 g (35%) of 1-benzyl-4-benzyloxymethyl-1,2,3,6-tetrahydropyridine was obtained as a yellow oil. MS (ISP): me/e=2.94 (C20H24NO+).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 2 hours
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel with hexane/ethyl acetate 9:1 to 3:1 as the eluent

Sources & evidence

ORD record
ord-dce454a6049446108ecb3623c38e1948
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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