Heptane → 1-Methyl-3-piperidyl alpha-Cyclopentyl-alpha-phenylethynyl-glycolate

HRID 358251

Reaction equation

HRID 358251 reaction equation
[Na].[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([OH:9])[CH2:4]1.CCCCCCC.[CH:17]1([C:22]([C:29]#[C:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([OH:28])[C:23](OCC)=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18]1>CCOCC>[CH:17]1([C:22]([C:29]#[C:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([OH:28])[C:23]([O:9][CH:5]2[CH2:6][CH2:7][CH2:8][N:3]([CH3:2])[CH2:4]2)=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 980163-Piperidinol, 1-methyl-HCID 5360545Sodium2×HCID 54429989Ethyl alpha-cyclopentyl-alpha-phenylethynylglycolate

Product 1

HCID 133711491-Methyl-3-piperidyl alpha-Cyclopentyl-alpha-phenylethynyl-glycolate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium (~0.05 g.) and 1-methyl-3-piperidinol (4.0 g., 0.035 mole) were refluxed in 250 ml. of dry n-heptane in a reaction flask equipped with a Dean-Stark trap until all of the sodium reacted. Then 6.5 g. (0.024 mole) of ethyl α-cyclopentyl-α-phenylethynylglycolate, undiluted, was added dropwise over a 0.25 hour period. The reaction mixture was subsequently refluxed for 20 hours, and about 30 ml. of solvent was collected toward the end of that period. The reaction mixture was kept overnight. No crystallization occurred during that time, but some tarry material was present and was filtered. Ether (acidic) and chloroform (basic) extracts were made of the filtrate as described previously. The chloroform extract yielded, after the solvent was stripped, 6.2 g. of a red-brown oil. The oil was dissolved in ether and petroleum ether (20°-40°) was added until turbidity was produced. The material was then placed in a freezer for four days and the product precipitated. It weighed 3.2 g., (39%) and melted at about 85° after being filtered and dried. The solid was recrystallized from 20°-40° petroleum ether. The first batch yielded off white crystals melting at 112°-113°.

Workup

  1. customreacted
  2. temperatureThe reaction mixture was subsequently refluxed for 20 hours
  3. customof solvent was collected toward the end of that period
  4. customNo crystallization
  5. filtrationwas filtered
  6. extractionThe chloroform extract
  7. customyielded
  8. customwas produced
  9. waitThe material was then placed in a freezer for four days
  10. customthe product precipitated
  11. filtration, (39%) and melted at about 85° after being filtered
  12. customdried
  13. customThe solid was recrystallized from 20°-40° petroleum ether

Sources & evidence

ORD record
ord-b63ac87e2a3b4a2f8f16293108dc6429
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Linked notes

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