Toluene → 1-Methyl-4-piperidyl alpha-Cyclopentyl-alpha-phenylethynylglycolate

HRID 358250Notes

Reaction equation

HRID 358250 reaction equation
[CH:1]1([C:6]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21][N:22]1[CH2:27]CC(O)[CH2:24][CH2:23]1.[Na].C1(C)C=CC=CC=1>CCCCCC.CCOCC>[CH:1]1([C:6]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:12])[C:7]([O:9][CH:10]2[CH2:24][CH2:23][N:22]([CH3:27])[CH2:21][CH2:11]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 660484-Piperidinol, 1-methyl-HCID 5360545SodiumHCID 54429989Ethyl alpha-cyclopentyl-alpha-phenylethynylglycolate

Product 1

HCID 133711481-Methyl-4-piperidyl alpha-Cyclopentyl-alpha-phenylethynylglycolate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

The reaction of ethyl α-cyclopentyl-α-phenylethynylglycolate (5.4 g., 0.02 mole), 1-methyl-4-piperidinol (3.5 g., 0.03 mole) and sodium (~0.05 g.) in about 85 ml. of toluene was carried out essentially as described in the preceding preparation. However, no solid precipitated upon the addition of 20°-40° petroleum ether at the end of the reflux period. The reaction mixture therefore was poured on ice and HCl and extracted with ether. The ether extracts were washed with dilute HCl. The washings and water layer were combined, made basic with sodium carbonate, and extracted with chloroform. Drying of the basic extract and subsequent distillation of the volatile compound in vacuo yielded a tarry residue which, when treated with ether and hexane gave 1.5 g. (22%) of crude product. The pure compound, m.p. 104°-105°, was obtained by recrystallization from hexane.

Workup

  1. customas described in the preceding preparation
  2. customHowever, no solid precipitated upon the addition of 20°-40° petroleum ether at the end of the reflux period
  3. additionThe reaction mixture therefore was poured on ice and HCl
  4. extractionextracted with ether
  5. washThe ether extracts were washed with dilute HCl
  6. extractionextracted with chloroform
  7. customDrying of the
  8. extractionbasic extract
  9. distillationsubsequent distillation of the volatile compound in vacuo
  10. customyielded a tarry residue which, when
  11. customgave 1.5 g

Sources & evidence

ORD record
ord-1a2fce2b78ad4943bd48c7e58418500f
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Reaction notes

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