Hydrochloric Acid → HCID 20295555, compound

HRID 1389881Notes

Reaction equation

HRID 1389881 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:19])[CH:12]=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[CH2:20]=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][CH:24]=1.Cl>C(O)(C)C>[CH3:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:9]([C:7]([CH:4]1[CH2:5][CH2:6][N:1]([CH:30]([CH3:20])[C:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)=[O:31])[CH2:2][CH2:3]1)=[O:8])=[CH:10][CH:11]=[CH:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 98284'-FluoroacetophenoneHCID 20295564HCID 20295564, compound

Product 1

HCID 20295555HCID 20295555, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolCatalyst

Procedure

A mixture of 25.5 g (0.1 mole) of 8-methyl-1-naphthyl 4-piperidyl ketone, 9 g (0.3 mole) of paraformaldehyde and 13.8 g (0.1 mole) of 4'-fluoroacetophenone in 100 ml of isopropyl alcohol containing 2 drops of concentrated hydrochloric acid is refluxed for 24 hours. The mixture is filtered and the filtrate concentrated to about 100 ml and cooled. The resulting precipitate is recrystallized from ethanol to give 2-[4-(8-methyl-1-naphthoyl)piperidyl]-1-(4-fluorophenyl)-1-propanone.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated to about 100 ml
  4. temperaturecooled
  5. customThe resulting precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-4f4941cfc1854133972c26c8bc4542a3
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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