Hydrazine hydrate (1:1) → 3-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amine

HRID 2043520Notes

Reaction equation

HRID 2043520 reaction equation
[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1.O.NN>CO.[Ni]>[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 44430852N,N-dimethyl-4-(5-nitro-1H-indol-3-yl)cyclohex-3-enamine

Product 1

HCID 574744603-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amineYield 98.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of compound 112 (0.21 g, 0.735 mmol) in dry methanol (5 mL) was treated with Ra—Ni (0.05 g) followed by hydrazine hydrate (0.22 mL, 7.359 mmol) at room temperature. The reaction was placed in a pre-heated oil bath and refluxed for 5 min. The reaction brought to room temperature, filtered through celite bed and washed with methanol (2×10 mL). The solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9) to obtain compound 113 (0.185 g, quantitative) as a foam. mp 63-65° C.; 1H NMR (DMSO-d6) δ 1.40-1.52 (m, 1H), 1.97-2.02 (m, 1H), 2.08-2.57 (m, 11H), 4.47 (s, 2H), 5.99 (brs, 1H), 6.47 (dd, 1H, J=1.8, 8.4 Hz), 6.99 (d, 1H, J=0.9 Hz), 7.04 (d, 1H, J=8.7 Hz), 7.13 (d, 1H, J=2.4 Hz), 10.55 (s, 1H); ESI-MS m/z (%): 256 (MH+, 100), 211 (41).

Workup

  1. customThe reaction was placed in a pre-heated oil bath
  2. temperaturerefluxed for 5 min
  3. custombrought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (2×10 mL)
  6. customThe solvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-b78110b66c3d4338810f6a1dadf0b165
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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