Hydrochloric Acid → HCID 20039785, compound

HRID 1762907Notes

Reaction equation

HRID 1762907 reaction equation
[ClH:1].[O:2]([CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[OH:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.N1CCCCC1.Cl>CO.CO.C(Cl)Cl.C(Cl)Cl.CCCCCC.[Pt]=O>[ClH:1].[O:2]([CH2:9][CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)[OH:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 8082PiperidineHCID 14201526HCID 14201526, compound

Product 1

HCID 20039785HCID 20039785, compoundYield 25.5%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

A solution of α-phenoxymethyl-2-pyridinemethanol hydrochloride (20.22 g, 0.08 mole) in 425 ml of methanol was hydrogenated for 2.5 hr in the presence of 1 g of platinum oxide at room temperature. TLC analysis (in 5% methanol-methylene chloride) showed that all the pyridine compound had been converted to the piperidine derivatives. Removal of methanol furnished an oil. The oil was dissolved in methylene chloride-hexane mixture and treated with ethereal hydrogen chloride. The resulting salt was triturated with acetone and recrystallized from methylenechloride-hexane-diethyl ether to give 5.28 g (25.5% of a white crystalline solid, m.p. 165°-171° C.

Workup

  1. customRemoval of methanol
  2. customfurnished an oil
  3. customThe resulting salt was triturated with acetone
  4. customrecrystallized from methylenechloride-hexane-diethyl ether

Sources & evidence

ORD record
ord-c571b611561b446fa9fbbc1b0915ea3e
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Reaction notes

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