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The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt. N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride

The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt. N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Propose a mechanism for the formation of (A)

The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt.
Transcribed Image Text:The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt.
N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride
Transcribed Image Text:N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride
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