Hydrochloric Acid → HCID 20394289, compound

HRID 261489Notes

Reaction equation

HRID 261489 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2F)([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].[ClH:19]>CN(C)C=O.C1C=CC=CC=1.CCOCC>[ClH:19].[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:8]2)[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 20394266HCID 20394266, compound

Product 1

HCID 20394289HCID 20394289, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

12.5 g of 1-methyl-4-(2-fluorobenzyl)-4-piperidinol dissolved in 50 ml of dimethylformamide and 20 ml of benzene are added to a stirred suspension at 120° C. of 2.3 g of a 57% oil dispersion of sodium hydride in 110 ml of dimethylformamide and 20 ml of benzene. The reaction mixture is stirred at 120° C. for 84 hours and then successively permitted to cool to ambient temperature, poured into 800 ml of ice-water and extracted with ether. The combined ether extracts were dried before the ether evaporated leaving a light yellow oil. The oil is dissolved in ether and converted to its hydrochloride salt with ethereal hydrogen chloride. The salt is recrystallized twice from an ethanol-ether mixture to provide the product, 2,3-dihydro-1'-methylspiro[benzofuran-2,4'-piperidine]hydrochloride, mp 248°-250° C.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ether
  3. dry with materialThe combined ether extracts were dried before the ether
  4. customevaporated
  5. customleaving a light yellow oil
  6. customThe salt is recrystallized twice from an ethanol-ether mixture

Sources & evidence

ORD record
ord-e40487c533ca4542bb530eea2beaf1e8
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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