1,4'-Bipiperidine → HCID 53663849, compound

HRID 975100Notes

Reaction equation

HRID 975100 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:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)[CH2:24][CH2:23][N:22]([C:25](=[O:35])[CH2:26][C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])[CH2:21]1)(=O)=O.C(#N)C>>[Cl:43][C:38]1[CH:37]=[C:36]([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:35])[CH2:26][C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])[CH2:21]2)[CH:41]=[CH:40][C:39]=1[Cl:42]

Participants

3

Reactant 2

HCID 786071,4'-BipiperidineHCID 86750415HCID 86750415, compound

Product 1

HCID 53663849HCID 53663849, compound

Procedure

In 30 ml of acetonitrile (R)-3-(2-methanesulfonyloxyethyl)-3-(3,4-dichlorophenyl)-1-[(2-chloro-6-fluorophenyl)acetyl]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 and 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
  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-9d28ccbe3ac24f8e8bf688c529bc4c43
Source dataset
uspto-grants-1997_03
Patent number
US05607947

Reaction notes

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