Hydrochloric Acid → 1-Methylpiperidin-4-yl 2-cyclohexyl-2-hydroxy-4-phenylbut-3-ynoate--hydrogen chloride (1/1)

HRID 358248Notes

Reaction equation

HRID 358248 reaction equation
[CH:1]1([C:7]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][N:23]1[CH2:28]CC(O)[CH2:25][CH2:24]1.[Na].[ClH:31]>C1(C)C=CC=CC=1.CCOCC>[ClH:31].[CH:1]1([C:7]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:13])[C:8]([O:10][CH:11]2[CH2:25][CH2:24][N:23]([CH3:28])[CH2:22][CH2:12]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 660484-Piperidinol, 1-methyl-HCID 5360545SodiumHCID 54432452HCID 54432452, compound

Product 1

HCID 162057371-Methylpiperidin-4-yl 2-cyclohexyl-2-hydroxy-4-phenylbut-3-ynoate--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

This ester was prepared by a method similar to the ones described above from the reaction of ethyl α-cyclohexyl-α-phenylethynyl-glycolate (4.3 g., 0.015 mole), 1-methyl-4-piperidinol (2.3 g., 0.020 mole) and sodium (~0.05 g.) in toluene. The chloroform extract of the basic phase of the reaction mixture, when stripped of volatile components in vacuo, yielded an oil. The oil was dissolved in dry ether and treated with HCl (gas) to give an oily solid. Recrystallization from a chloroform-benzene mixture gave about 0.6 g. (10%) of the desired hydrochloride, m.p. about 198°-200°.

Workup

  1. extractionThe chloroform extract of the basic phase of the reaction mixture, when
  2. customyielded an oil
  3. customto give an oily solid
  4. customRecrystallization from a chloroform-benzene mixture
  5. customgave about 0.6 g

Sources & evidence

ORD record
ord-60ecc5323c9c494d9eed1ee618e8b358
Source dataset
uspto-grants-1984_08
Patent number
US04465834

Reaction notes

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