Triethylamine → 4-(4-Acryloylpiperazin-1-yl)-2-fluorobenzonitrile

HRID 2354566Notes

Reaction equation

HRID 2354566 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:23]([N:13]1[CH2:12][CH2:11][N:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=2)[CH2:15][CH2:14]1)(=[O:26])[CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 187600452-Fluoro-4-(piperazin-1-YL)benzonitrile

Product 1

HCID 684518974-(4-Acryloylpiperazin-1-yl)-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-fluoro-4-(piperazin-1-yl)-benzonitrile (0.53 g, 2.56 mmol) and triethylamine (0.5 ml, 3.59 mmol) in CH2Cl2 (13 ml) is added dropwise to a cooled solution (0-5° C.) of acryloyl chloride (0.25 ml, 3.15 mmol) in CH2Cl2 (3 ml). After complete addition, the mixture is stirred at rt for 1 h, sat. aq. Na2CO3 solution is added and stirring is continued for 20 min. The organic layer is separated off, dried over Na2SO4 and evaporated. Upon addition of AcOEt, 4-(4-acryloyl-piperazin-1-yl)-2-fluoro-benzonitrile crystallizes out, is filtered off, washed with AcOEt and air-dried.

Workup

  1. additionAfter complete addition
  2. stirringstirring
  3. waitis continued for 20 min
  4. customThe organic layer is separated off
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. additionUpon addition of AcOEt, 4-(4-acryloyl-piperazin-1-yl)-2-fluoro-benzonitrile
  8. customcrystallizes out
  9. filtrationis filtered off
  10. washwashed with AcOEt
  11. customair-dried

Sources & evidence

ORD record
ord-db9693543d4f4ca2a023bfa583b96b6d
Source dataset
uspto-grants-2010_07
Patent number
US07754719B2

Reaction notes

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