Hydrochloric Acid → HCID 15631322, compound

HRID 1905389Notes

Reaction equation

HRID 1905389 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]3[C:9]=2[CH2:10][CH2:11][CH2:12][NH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:19].CCCCCC>ClCCl.CO>[ClH:19].[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]3[C:9]=2[CH2:10][CH2:11][CH2:12][NH:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8058Hexane2×HCID 15631321HCID 15631321, compound

Product 1

HCID 15631322HCID 15631322, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 199.8 mg (0.83 mmol) of 1,2,3,4-tetrahydro-5-(phenylmethyl)-8-quinolinol in 2 ml of dichloromethane was treated with 1 ml of hydrogen chloride-saturated dichloromethane. The addition of 15 ml of hexane resulted in the precipitation of a yellow solid. Microanalysis indicated that this material contained approximately 10% of the free base of the starting material. This mixture was taken up in 1 ml of methanol and treated with 0.5 ml of hydrogen chloride-saturated methanol, then 2 ml of dichloromethane and 10 ml of hexane. Evaporation gave a pale yellow, waxy solid, which was triturated with 5 ml of dichloromethane and 5 ml of hexane. Filtration provided 147.6 mg of the title compound as a pale yellow solid:melting point 219°-221° C. (decomposition 190°-219° C.).

Workup

  1. customresulted in the precipitation of a yellow solid
  2. customEvaporation
  3. customgave a pale yellow, waxy solid, which
  4. customwas triturated with 5 ml of dichloromethane and 5 ml of hexane
  5. filtrationFiltration

Sources & evidence

ORD record
ord-36949097e2b1404798d2cdf1f040e50c
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

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