Piperidine → HCID 86735973, compound

HRID 2420239Notes

Reaction equation

HRID 2420239 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C@@H:12]([OH:21])[C@@H:11]([N:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[CH2:10]2)[CH2:7][CH2:6]3.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O>[N:29]1([C@H:2]2[CH2:19][C@@:18]3([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][C@H:11]([N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[C@@H:12]3[OH:21])[CH2:4][C@@H:3]2[OH:1])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86735970HCID 86735970, compound

Product 1

HCID 86735973HCID 86735973, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.8 g (0.03 mole) of 2α,3α-epoxy-17β-hydroxy-16β-N-methyl-piperazino-5α-androstane (Example 10) are dissolved in 168 ml (1.65 moles) of piperidine and 24 ml of water, whereafter the reaction mixture is heated in a bomb tube of 72 hours at a temperature of 140° C. After the reaction is accomplished the reaction mixture is evaporated at reduced pressure. The residue is stirred in acetonitrile, filtered and the product above the filter is heated under reflux in acetonitrile. The crystallized product is filtered and dried. Yield: 12.4 g (69.0%) of 2β-piperidino-16β-N-methyl-piperazino-3α,17β-dihydroxy-5α-androstane; m.p. 154°-156° C; [α]D25 = +84.5° (c = 1 in chloroform).

Workup

  1. customis evaporated at reduced pressure
  2. filtrationfiltered
  3. temperaturethe product above the filter is heated
  4. temperatureunder reflux in acetonitrile
  5. filtrationThe crystallized product is filtered
  6. customdried

Sources & evidence

ORD record
ord-657f4411a8704a128bd70875529b842d
Source dataset
uspto-grants-1978_08
Patent number
US04110326

Reaction notes

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