1,4-Dibromobutane → 4-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzonitrile

HRID 425961Notes

Reaction equation

HRID 425961 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:8][CH2:9][CH2:10][CH2:11]Br.[NH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]1[NH:20][C:21]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]>C(#N)C>[Cl:29][C:27]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([NH:20][C@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@@H:14]2[N:13]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:28]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 667037922-{[(1S,2S)-2-aminocyclohexyl]amino}-4-chlorobenzonitrile

Product 1

HCID 667036344-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate and 1,4-dibromobutane were added to an acetonitrile solution of 2-{[(1S*,2S*)-2-aminocyclohexyl]amino}-4-chlorobenzonitrile, followed by heating under reflux for 2 days. By post-treating the reaction liquid, 4-chloro-2-{[(1S*,2S*)-2-pyrrolidin-1-ylcyclohexyl]amino}benzonitrile was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 days
  3. additionBy post-treating
  4. customthe reaction liquid

Sources & evidence

ORD record
ord-ab198210ab394fe1b73f65e35dc883b8
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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