1-Benzyl-4-piperidone → 4-(2H-1,3-Benzodioxol-5-yl)-1-benzylpiperidin-4-ol

HRID 1004950Notes

Reaction equation

HRID 1004950 reaction equation
[Mg].Br[C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>O1CCCC1>[O:7]1[C:6]2[CH:10]=[CH:11][C:3]([C:22]3([OH:25])[CH2:23][CH2:24][N:19]([CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][CH2:21]3)=[CH:4][C:5]=2[O:9][CH2:8]1

Participants

6

Reactant 4

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5462224Magnesium

Product 1

HCID 221280344-(2H-1,3-Benzodioxol-5-yl)-1-benzylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To 1.46 g of magnesium shavings, which had previously been covered with tetrahydrofuran, was added dropwise a solution of 12.06 g (60 mmol) of 5-bromo-benzo[1,3]dioxol in 30 ml of absolute tetrahydrofuran, followed by 11.35 g (60 mmol) of 1-benzyl-4-piperidone. The reaction mixture was stirred at 50° C. for 1 hour, then poured on to ice and ammonium chloride solution. The 4-benzo[1,3]dioxol-5-yl-1-benzyl-piperidin-4-ol formed was extracted with ethyl acetate and crystallized upon concentration of the solution. There were obtained 10.85 g (58% of theory) of white crystals; m.p.: 144° C.

Sources & evidence

ORD record
ord-481309fe81474a30be03ed5589a8b2b5
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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