Formaldehyde → 3-[3(S)-Ethyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol

HRID 65221Notes

Reaction equation

HRID 65221 reaction equation
Cl.Cl.[CH:3]([C@@H:5]1[C@H:10]([CH2:11][CH2:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[OH:14])[CH2:9][CH2:8][NH:7][CH2:6]1)=[CH2:4].[OH-].[Na+].C=O.C1(C)C(CO)=CC=CC=1.C(NCC)C>O>[CH2:3]([C@H:5]1[C@H:10]([CH2:11][CH2:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[OH:14])[CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium Hydroxide2×HCID 30682314-Quinolinemethanol, alpha-(2-(3-ethenyl-4-piperidinyl)ethyl)-6-methoxy-, dihydrochloride, (3R-(3-alpha,4-alpha(S*)))-HCID 70380594HCID 70380594, compound

Product 1

HCID 57471123-[3(S)-Ethyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6 g of 3-[3(R)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol dihydrochloride, 15 ml of a normal aqueous solution of sodium hydroxide, 1.2 ml of a 0.4% aqueous solution of formaldehyde and 60 ml of water was heated at 120° C. for 24 hours in an autoclave. After cooling, the reaction medium was made alkaline by addition of sodium hydroxide lye and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue obtained was subjected to high pressure liquid chromatography (support: silica gel; eluant: 100/7.5/3.75 toluene-methanol-diethylamine mixture). The separated fractions containing the desired product were evaporated. There was thus recovered 2.6 g of an oil which, by the action of HCl in ethanol, was converted into the dihydrochloride. After three recrystallizations of this last product in ethanol, 0.7 g of 3-[3(S)-ethenyl 4(R)-piperidyl]-1-(6-methoxy-4-quinolyl)-1(S)-propanol were obtained in the form of the dihydrochloride melting at 204° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe oily residue obtained

Sources & evidence

ORD record
ord-6b4936d098784889950b2ef5ce10dd93
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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