Hydrochloric Acid → HCID 9800314, compound

HRID 1004439Notes

Reaction equation

HRID 1004439 reaction equation
[ClH:1].[C:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[CH2:21][CH2:20][CH2:19]2.[CH2:27]=O>C(O)(C)C.C1(C)C=CC=CC=1>[ClH:1].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[CH:21]([CH2:27][N:11]1[CH2:10][CH2:9][CH:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]1)[CH2:20][CH2:19]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 141126-Methoxy-alpha-tetraloneHCID 698734-Phenylpiperidine

Product 1

HCID 9800314HCID 9800314, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent2×

Procedure

Concentrated hydrochloric acid (4.9 mL) was added to a solution of 4-phenylpiperidine (9.38 g, 58.2 mmol) in isopropanol (60 mL) at 10-15° C. followed by the sequential addition of 6-methoxy-1-tetralone (9.76 g, 55.4 mmol), 37% aqueous formaldehyde (5.72 g) and 60 mL isopropanol. The mixture was refluxed for 1 hour, diluted with toluene, concentrated and the residue recrystallized sequentially from acetone and ethanol to afford the title compound as a white solid (5 g), mp 177-8° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. customthe residue recrystallized sequentially from acetone and ethanol

Sources & evidence

ORD record
ord-f41c0d80c41d413393fba62857131a61
Source dataset
uspto-grants-2000_04
Patent number
US06048877

Reaction notes

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