2-Chloroethyl isocyanate → HCID 66855252, compound

HRID 2400760Notes

Reaction equation

HRID 2400760 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[NH2:24])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl[CH2:26][CH2:27][N:28]=[C:29]=[O:30].[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[N:24]3[CH2:26][CH2:27][NH:28][C:29]3=[O:30])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 66854400HCID 66854400, compound

Product 1

HCID 66855252HCID 66855252, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1-[(E)-3-(4-chloro-phenyl)-allyl]-4-(5-fluoro-2-amino-phenyl)-piperazine (1.0 g, Example 3, Step B) in tetrahydrofuran (10 ml) at 0° C. was added 2-chloroethylisocyanate (327 mg) and the resulting solution was stirred under nitrogen at room temperature for 18 hours. The residue was dissolved in a minimum volume of tetrahydrofuran, then added to a suspension of sodium hydride (146 mg, 50% in oil) in tetrahydrofuran (10 ml). The reaction mixture was stirred at room temperature for 3 hours, concentrated under reduced pressure, then triturated with diethyl ether to afford 1-(2-{4-[(E)-3-(4-chloro-phenyl)-allyl]-piperazin-1-yl}-4-fluoro-phenyl)-imidazolidin-2-one (677 mg) as white crystals. M.p. 170-172° C.; 1H NMR (400 MHz, CDCl3) 2.7 (m, 4H), 3.11 (m, 4H), 3.26 (d, J=6.8 Hz, 2H), 3.63 (t, J=5.7 Hz, 2H), 3.99 (t, J=5.7 Hz, 2H), 5.12 (br s, 1H), 6.32 (dt, J=15.6, 6.8 Hz, 1H), 6.57 (d, J=15.6 Hz, 1H), 6.82 (m, 2H), 7.3-7.4 (m, 4H); MS (ES+) 415/417 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-944bec69006f4d9089c74dbd6b4be925
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

Loading…