Ammonium Chloride → HCID 13755886, compound

HRID 867873Notes

Reaction equation

HRID 867873 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH:10]([CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[CH3:23][Mg]I.[Cl-].[NH4+]>C(OCC)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:23])([OH:15])[CH:10]([CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 13755882HCID 13755882, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 13755886HCID 13755886, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Tert-butyl-2-piperidinomethyl-1,2,3,4-tetrahydronaphthalen-1-one (4.4 g, 0.015 mol) in diethyl ether (40 ml) was added to an ethereal solution of methylmagnesium iodide [prepared from methyl iodide (1.9 ml, 0.03 mol) and magnesium (0.72 g, 0.03 mol)] at such a rate as to maintain reflux. It was refluxed for 1 hour, cooled and treated with saturated ammonium chloride solution (100 ml) and refluxed for 30 minutes. The ether was separated and the aqueous extracted with further ether, the combined extracts were dried over magnesium sulphate and evaporated to give a solid residue. Purification by column chromatography using silica gel with ethyl acetate: petroleum 60°-80°, 3:7 gave 6-tert-butyl-1-methyl-2-piperidinomethyl-1,2,3,4-tetrahydronaphthalen-1-ol (3.9 g, 82% yield) a white solid melting at 113°-4°. 6-tert-butyl-1-methyl-2-piperidinomethyl-1,2,3,4-tetrahydronaphthalen-1-ol (3.7 g, 0.012 mol) was refluxed in dilute sulphuric acid (50 ml, 10%) for 45 minutes. After cooling it was neutralized with sodium hydroxide, extracted with ether, dried over magnesium sulphate and evaporated under reduced pressure to give the title compound (3.5 g, 98% yield) as a clear oil.

Workup

  1. temperatureto maintain
  2. temperaturereflux
  3. temperatureIt was refluxed for 1 hour
  4. temperaturecooled
  5. temperaturerefluxed for 30 minutes
  6. customThe ether was separated
  7. extractionthe aqueous extracted with further ether
  8. dry with materialthe combined extracts were dried over magnesium sulphate
  9. customevaporated
  10. customto give a solid residue
  11. customPurification by column chromatography

Sources & evidence

ORD record
ord-1e473786d0084fc9ab1a3ecfe8629bb4
Source dataset
uspto-grants-1988_10
Patent number
US04777176

Reaction notes

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