Hydrochloric Acid → HCID 21462988, compound

HRID 1940535Notes

Reaction equation

HRID 1940535 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Mg].[C:13]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)(=[O:15])[CH3:14].Cl>O1CCCC1.C(OCC)C>[OH:22][C:19]1([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)[CH2:20][CH2:21][N:16]([C:13](=[O:15])[CH3:14])[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 113722-BromonaphthaleneHCID 122563N-Acetyl-4-piperidoneHCID 5462224Magnesium

Product 1

HCID 21462988HCID 21462988, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

2-Bromonaphthalene (24.75 g, 0.12 mol) in tetrahydrofuran (180 ml) was slowly added to magnesium (2.9 g, 0.12 mol) in tetrahydrofuran (20 ml) and the mixture stirred at room temperature for one hour. The resultant solution was slowly added to 1-acetyl-4-piperidone (16.9 g, 0.12 mol) in tetrahydrofuran (200 ml) at -78° C., and then allowed to stir to room temperature. The white suspension formed was hydrolysed with hydrochloric acid (120 ml, 1M) and the organic layer removed and concentrated in vacuo. The residue was taken up in dichloromethane, dried (MgSO4), and concentrated to leave a clear oil. Trituration of this oil with diethyl ether gave 1-(4-hydroxy-4-naphthalen-2-yl-piperidin-1-yl)ethanone (13.92 g, 43%) as a white solid; δH (CDCl3) 1.90 (4H, m, 2× piperidinyl CH2), 2.10 (2H, m, piperidinyl CH2), 2.15 (3H, s, COCH3), 3.20 (1H, m, piperidinyl H), 3.70 (1H, m, piperidinyl H), 4.60 (1H, br m, OH), 7.50 (2H, m, ArH), 7.60 (1H, dd, J 9.6, 1.6 Hz, ArH), and 7.90 (4H, m, ArH).

Workup

  1. stirringto stir to room temperature
  2. customThe white suspension formed
  3. customthe organic layer removed
  4. concentrationconcentrated in vacuo
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto leave a clear oil

Sources & evidence

ORD record
ord-4fcf12b333864009899aaa0818640adc
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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