Ethanol → HCID 12822305, compound

HRID 1112289Notes

Reaction equation

HRID 1112289 reaction equation
Cl[CH2:2][CH:3]1[CH2:7][N:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:5](=[O:14])[C:4]1([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2([OH:46])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:36][CH:35]=1.C(O)C>CO.C(Cl)(Cl)Cl.CO>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2([OH:46])[CH2:41][CH2:42][N:43]([CH2:2][CH:3]3[CH2:7][N:6]([CH:8]4[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]4)[C:5](=[O:14])[C:4]3([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:44][CH2:45]2)=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 128222931-Cyclohexyl-4-chloromethyl-3,3-diphenyl-2-pyrrolidinone

Product 1

HCID 12822305HCID 12822305, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 39 g. (0.106 mole) of 4-chloromethyl-1-cyclohexyl-3,3-diphenyl-2-pyrrolidinone, 58.5 g. (0.424 mole) of finely ground potassium carbonate, and 22.5 g. (0.106 mole) of 4-(4-chlorophenyl)-4-hydroxypiperidine in 300 ml. of ethanol was heated to 200° C. in a steel bomb for 66 hrs. During the heating the bomb was continuously rotated to produce mild stirring. The contents were filtered and the filtrate concentrated. The residue was heated in 250 ml. of ethylacetate and allowed to stand at room temperature overnight. The mixture was filtered. The filtrate was extracted with dilute hydrochloric acid and dilute sodium hydroxide. The ethylacetate was concentrated and the residue dissolved in ethanol and allowed to stand overnight. The resulting mixture was filtered and the filtrate concentrated. The residue was chromatographed on a 4.5 × 60 cm. silica gel column. The product was obtained from the column using a chloroform-methanol eluate containing increasing amounts of methanol. The product after isolation and crystallization from isopropanol melted at 222°-225° C.

Workup

  1. additionA mixture of 39 g
  2. customto produce mild stirring
  3. filtrationThe contents were filtered
  4. concentrationthe filtrate concentrated
  5. temperatureThe residue was heated in 250 ml
  6. filtrationThe mixture was filtered
  7. extractionThe filtrate was extracted with dilute hydrochloric acid and dilute sodium hydroxide
  8. concentrationThe ethylacetate was concentrated
  9. dissolutionthe residue dissolved in ethanol
  10. waitto stand overnight
  11. filtrationThe resulting mixture was filtered
  12. concentrationthe filtrate concentrated
  13. customThe residue was chromatographed on a 4.5 × 60 cm
  14. customThe product was obtained from the column
  15. additioncontaining
  16. customThe product after isolation and crystallization from isopropanol melted at 222°-225° C.

Sources & evidence

ORD record
ord-4616da6b6c0b4ec5a999e703401ab0ea
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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