Sodium Hydroxide → HCID 22729078, compound

HRID 1940536Notes

Reaction equation

HRID 1940536 reaction equation
O[C:2]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH2:7][CH2:6][N:5](C(=O)C)[CH2:4][CH2:3]1.[OH-].[Na+]>Cl>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21462988HCID 21462988, compound

Product 1

HCID 22729078HCID 22729078, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-(4-Hydroxy-4-naphthalen-2-yl-piperidin-1-yl)ethanone (3.40 g, 13 mmol) was dissolved in hydrochloric acid (50 ml, 6M) and the solution refluxed for 12 hours. The resultant mixture was cooled in ice, basified with sodium hydroxide solution (32 ml, 10M) and extracted with dichloromethane (2×100 ml). The extracts were combined, dried (MgSO4) and concentrated to give 4-naphthalen-2-yl-1,2,3,6-tetrahydropyridine (2.12 g, 78% ) as a tan solid; δH (CDCl3) 2.60 (2H, m, tetrahydropyridinyl CH2), 3.20 (2H, t, J 5.6 Hz, tetrahydropyridinyl CH2), 3.60 (2H, m, tetrahydropyridinyl CH2), 6.30 (1H, m, CH=CR), 7.45 (2H, m, ArH), 7.60 (1H, dd, J 8.4, 1.4 Hz, ArH), and 7.80 (4H, m, ArH).

Workup

  1. temperaturethe solution refluxed for 12 hours
  2. extractionextracted with dichloromethane (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a7474bcc409d4c98aecb7454ee4d5cf3
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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