Dichloromethane → HCID 66854859, compound

HRID 2400758Notes

Reaction equation

HRID 2400758 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.F[C:25](F)(F)[C:26](O)=O.Cl[CH2:32][Cl:33]>>[Cl:33][C:32]1[CH:18]=[CH:19][C:14](/[CH:25]=[CH:26]/[CH2:6][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[N+:21]([O-:23])=[O:22])[CH2:12][CH2:13]2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22272537tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 66854859HCID 66854859, compound

Procedure

A solution of 4-(5-fluoro-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, prepared from 2,4-difluoronitrobenzene as described in Example 1, Step A) in dichloromethane (80 ml) was treated with trifluoroacetic acid (23 ml) for 24 hours at room temperature. The reaction mixture was concentrated in vacuo. The residue was dissolved in acetonitrile (100 ml), diisopropylethylamine (27 ml) and 4-chloro-cinnamyl chloride (6.8 g) were added. The solution was stirred for 17 hours at room temperature, the solvent was removed in vacuo and the residue was subjected to silica gel chromatography (cyclohexane:ethyl acetate 1:1) to afford 1-[(E)-3-(4-chloro-phenyl)-allyl]-4-(5-fluoro-2-nitro-phenyl)-piperazine (10.5 g); 1H NMR (400 MHz, CDCl3) 2.7 (t, J=8 Hz, 4H), 3.1 (t, J=8 Hz, 4H), 3.2 (d, J=9 Hz, 2H), 6.2 (dt, J=18, 9 Hz, 1H), 6.5 (d, J=18 Hz, 1H), 6.6 (dt, J=1.0, 7.0 Hz, 1H), 6.7 (dd, J=1.0, 10 Hz, 1H), 7.2-7.3 (m, 4H), 7.8 (d, J=7.0, 10.0 Hz, 1H); MS (ES+) 151/153, 376/378 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in acetonitrile (100 ml)
  3. additiondiisopropylethylamine (27 ml) and 4-chloro-cinnamyl chloride (6.8 g) were added
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-28f8a41aecb3471e9cc513e95acc9ab1
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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