1-Cyclohexylpiperazine → HCID 54373145, compound

HRID 975089Notes

Reaction equation

HRID 975089 reaction equation
[CH:1]1([N: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][N:7]([CH: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 872981-CyclohexylpiperazineHCID 86750408HCID 86750408, compound

Product 1

HCID 54373145HCID 54373145, compound

Procedure

In 30 ml of acetonitrile (S)-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 1-cyclohexylpiperazine. 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-a0bef2235363480a8cd1900fa08dde27
Source dataset
uspto-grants-1997_03
Patent number
US05607947

Reaction notes

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