4-Benzyl-4-piperidinol → HCID 22628342, compound

HRID 278450Notes

Reaction equation

HRID 278450 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH:14]([CH2:19]Br)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([C:28]1([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:21]([C:28]1([OH:34])[CH2:33][CH2:32][N:31]([CH2:19][CH:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[O:15]2)[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 981524-Benzyl-4-piperidinolHCID 22628333HCID 22628333, compound

Product 1

HCID 22628342HCID 22628342, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(RS)-6-Benzyloxy-2-bromomethyl-chroman (0.52 g, 1.56 mmol) and 4-(benzyl)-piperidin-4-ol (0.66 g, 3.43 mmol) in toluene (20 ml) was refluxed for 18 hr under argon. After removal of the solvent the crude mixture was chromatographed over SiO2 (Merck 230-400 mesh) CH2Cl2—MeOH—NH4OH (100:5:0.25) to afford the title compound (RS)-4-benzyl-1-(6-benzyloxy-chroman-2-ylmethyl)-piperidin-4-ol as a yellow oil (0.6 g, 1.35 mmol, 86%), MS: m/e=444.5 (M+H+).

Workup

  1. customAfter removal of the solvent the crude mixture
  2. customwas chromatographed over SiO2 (Merck 230-400 mesh) CH2Cl2—MeOH—NH4OH (100:5:0.25)

Sources & evidence

ORD record
ord-aff704471ab64c5ebcb314e96099941e
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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