Sodium Dithionite → HCID 66854400, compound

HRID 2400759Notes

Reaction equation

HRID 2400759 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[N+:24]([O-])=O)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[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[NH2:24])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 66854859HCID 66854859, compound

Product 1

HCID 66854400HCID 66854400, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of the compound obtained in Step A (8.0 g) in ethanol (66 ml) and water (80 ml) at 60° C. was added sodium dithionite (11 g). The resulting mixture was stirred at 60° C. for 1 hour then ethanol was removed in vacuo. The suspension was extracted three times with ethyl acetate, the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was filtered on silica gel (eluent ethyl acetate) to afford 1-[(E)-3-(4-chloro-phenyl)-allyl]-4-(5-fluoro-2-amino-phenyl)-piperazine (4.1 g). 1H NMR (400 MHz, CDCl3) 2.6 (m, 4H), 2.9 (m, 4H), 3.2 (d, J=9 Hz, 2H), 3.7 (m, 2H), 6.2 (dt, J=18, 9 Hz, 1H), 6.5 (d, J=18 Hz, 1H), 6.6 (m, 2H), 6.7 (d, J=10 Hz, 1H), 7.2-7.3 (m, 4H); MS (ES+) 151/153, 346/348 (M+H+).

Workup

  1. customethanol was removed in vacuo
  2. extractionThe suspension was extracted three times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationThe residue was filtered on silica gel (eluent ethyl acetate)

Sources & evidence

ORD record
ord-00da168cffd14318a558486eeb409f7e
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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