1,4'-Bipiperidine → HCID 53641329, compound

HRID 975103Notes

Reaction equation

HRID 975103 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(O[CH2:18][CH2:19][C@:20]1([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[CH2:24][CH2:23][N:22]([C:25](=[O:36])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([CH3:35])[CH3:34])[CH:27]=2)[CH2:21]1)(=O)=O.C(#N)C>>[C:37]1([C@:20]2([CH2:19][CH2:18][N:10]3[CH2:11][CH2:12][CH:7]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:8][CH2:9]3)[CH2:24][CH2:23][N:22]([C:25](=[O:36])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([CH3:34])[CH3:35])[CH:27]=3)[CH2:21]2)[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 786071,4'-BipiperidineHCID 86750419HCID 86750419, compound

Product 1

HCID 53641329HCID 53641329, compound

Procedure

In 30 ml of acetonitrile (S)-3-(2-methanesulfonyloxyethyl)-3-(1-naphthyl)-1-(3-isopropoxybenzoyl)pyrrolidine (3.17 g), prepared as described, supra, is mixed with an equimolar amount of 4-(piperidin-1-yl)piperidine. The reaction mixture is then heated to reflux and refluxed for about ten hours. The mixture is then concentrated under vacuum an the residue is taken up in methylene chloride and washed with a 3N solution of hydrochloric acid, followed by a wash with brine. The organic fraction is dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue precipitates from an acetone/diethyl ether mixture to give the desired title product.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux
  3. temperaturerefluxed for about ten hours
  4. concentrationThe mixture is then concentrated under vacuum an the residue
  5. washwashed with a 3N solution of hydrochloric acid
  6. washa wash with brine
  7. dry with materialThe organic fraction is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue precipitates from an acetone/diethyl ether mixture

Sources & evidence

ORD record
ord-3623c142c0f2468d9d86ef92e6e785e6
Source dataset
uspto-grants-1997_03
Patent number
US05607947

Reaction notes

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