4-Benzhydrylpiperidine → 4-[6-(4-Benzhydrylpiperidino)hexyl]-3,5-dioxomorpholine

HRID 1395474Notes

Reaction equation

HRID 1395474 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:22](=[O:23])[CH2:21][O:20][CH2:19][C:18]2=[O:24])(=O)=O)=CC=1.[CH:26]([CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)(C)(C)C>[CH:26]([CH:39]1[CH2:44][CH2:43][N:42]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:18](=[O:24])[CH2:19][O:20][CH2:21][C:22]2=[O:23])[CH2:41][CH2:40]1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 882784-BenzhydrylpiperidineHCID 127961946-(3,5-Dioxomorpholino)hexyl p-toluenesulfonate

Product 1

HCID 127961974-[6-(4-Benzhydrylpiperidino)hexyl]-3,5-dioxomorpholineYield 149.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of 9.75 grams (26.39 millimoles) of 6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate (prepared as described in Example IX) in 160 milliliters of warm tertiary butyl alcohol was added portionwise at temperatures in the range of 30°-32° C. over a period of about 23 minutes, 63 grams (26.38 millimoles) of 4-benzhydrylpiperidine in 160 milliliters of tertiary-butyl alcohol. The reaction mixture was heated at reflux temperature for about 22 hours and thereafter the solvent removed by vaporization to obtain 17.7 grams of a 4-[6-(4-benzhydrylpiperidino)hexyl]-3,5-dioxomorpholine product as a yellow oil. Crystallization (twice) from ethyl acetate produced 4.19 grams of white crystals, m.p., 121°-124.5° C. and having NMR, UV and IR spectral characteristics appropriate for the product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for about 22 hours
  3. customthe solvent removed by vaporization

Sources & evidence

ORD record
ord-b7c8bd35171e4ad395af4c0b6b01f107
Source dataset
uspto-grants-1980_05
Patent number
US04203991

Reaction notes

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