Acetic Acid → HCID 86735972, compound

HRID 2420240Notes

Reaction equation

HRID 2420240 reaction equation
[N:1]1([C@H:7]2[CH2:24][C@@:23]3([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]4[C@@H:22]3[CH2:21][CH2:20][C@@:18]3([CH3:19])[C@H:14]4[CH2:15][C@H:16]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[C@@H:17]3[OH:26])[CH2:9][C@@H:8]2[OH:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:35](OC(=O)C)(=[O:37])[CH3:36].O.[OH-].[Na+].[C:45](O)(=[O:47])[CH3:46]>[Cl-].[Zn+2].[Cl-]>[N:1]1([C@H:7]2[CH2:24][C@@:23]3([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]4[C@@H:22]3[CH2:21][CH2:20][C@@:18]3([CH3:19])[C@H:14]4[CH2:15][C@H:16]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[C@@H:17]3[O:26][C:35](=[O:37])[CH3:36])[CH2:9][C@@H:8]2[O:34][C:45](=[O:47])[CH3:46])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 176Acetic Acid2×HCID 962WaterHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 86735973HCID 86735973, compound

Product 1

HCID 86735972HCID 86735972, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

3 g (0.0063 mole) of 2β-piperidino-16β-N-methyl-piperazino-3α,17β-dihydroxy-5α-androstane (Example 11) are dissolved in the mixture of 13 ml of acetic acid anydride and 1 ml of glacial acetic acid, whereafter 0.3 g of zinc chloride is given to the solution. The reaction mixture is stirred for 12 hours, whereafter the excess acetic acid anhydride is decomposed by adding 40 ml of water. The solution is cooled to 0° to 5° C and 15% aqueous sodium hydroxide solution is added at the same temperature until the pH achieves the value of 9-10. The precipitated fluffy substance is immediately extracted with ether. The ether extract is washed with an aqueous solution saturated with sodium chloride until a neutral state is achieved. The layers are separated, the ether layer is dried over sodium sulfate and filtered. The filtrate is treated with 3 g of decolorizing silica gel, the mixture is filtered and evaporated to dryness. The product is crystallized from the residue by trituration with n-hexane, filtered and dried. Yield: 2.6 g (73.5%) of 2β-piperidino-16β-N-methyl-piperazino-3α,17β-diacetoxy-5α-androstane; m.p. 95°-98° C; [α]D25 = +33.9° (c = 1 in chloroform).

Workup

  1. temperatureThe solution is cooled to 0° to 5° C
  2. extractionThe precipitated fluffy substance is immediately extracted with ether
  3. extractionThe ether extract
  4. washis washed with an aqueous solution saturated with sodium chloride until a neutral state
  5. customThe layers are separated
  6. dry with materialthe ether layer is dried over sodium sulfate
  7. filtrationfiltered
  8. additionThe filtrate is treated with 3 g of decolorizing silica gel
  9. filtrationthe mixture is filtered
  10. customevaporated to dryness
  11. customThe product is crystallized from the residue by trituration with n-hexane
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-c3e58cba69d34346baed0431846c7dea
Source dataset
uspto-grants-1978_08
Patent number
US04110326

Reaction notes

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