4-Bromophenylhydrazine hydrochloride → HCID 18398764, compound

HRID 1018918Notes

Reaction equation

HRID 1018918 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]1([C:17](=O)[CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C.ClCCl.CO.N>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:18]2[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 205541-Butanone, 1-phenyl-4-(1-piperidinyl)- (9CI)

Product 1

HCID 18398764HCID 18398764, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584172Ammonia methanol dichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4-Bromophenylhydrazine hydrochloride (1.45 g, 6.5 mmol) and 1-phenyl-4-(1-piperidinyl)butan-1-one (1.50 g, 6.5 mmol) were dissolved in ethanol (10 ml) and stirred at 25° C. for 4 hours. The solid was filtered and washed with ethanol and ether. The white product was dissolved in trifluoroacetic acid (10 ml) and heated at 70° C. for 2 hours. The reaction mixture was basified with saturated potassium carbonate solution and extracted into ethyl acetate. The organic phase was washed with brine, dried (sodium sulphate) and evaporated to give a yellow oil. Chromatography on silica gel with dichloromethane-methanol-ammonia (98:2:0.2) as eluent yielded the title compound (0.51 g, 20%) as a white solid. Oxalate salt, white crystals, mp 121-122° C. (from methanol/ether) (Found: C, 58.07; H, 5.23; N, 6.01. C21H23BrN2. C2H2O4. 0.1H2O requires C, 58.14; H, 5.35; N, 5.90%); δH (360 MHz, dG-DMSO) 1.5-1.6 (2H, m, piperidine H-4), 1.7-1.8 (4H, m, piperidine H-3), 3.1-3.3 (8H, m, CH2), 7.2 (1H, dd, J 2 and 8, indole H-6), 7.3 (1H, d, J 8, indole H-7), 7.4 (1H, t, J 7, Ar H-4), 7.5 (2H, t, J 7, Ar H-3), 7.6 (2H, d, J 7, Ar H-2), 7.8 (1H, ds, J 2, indole H-4), 11.6 (1H, br s, indole NH); m/z (ES+) 383 ( M++H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethanol and ether
  3. dissolutionThe white product was dissolved in trifluoroacetic acid (10 ml)
  4. temperatureheated at 70° C. for 2 hours
  5. extractionextracted into ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried (sodium sulphate)
  8. customevaporated
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-53de5ec4aaa743f68fa93ab5607442f1
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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