Hydrazine hydrate (1:1) → 5'-(3-Chlorophenyl)spiro[cyclohexane-1,3'-[3h]indol]-2'-amine

HRID 9338Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][C:11]23[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2N[OH:23])[CH:5]=[CH:6][CH:7]=1.O.[NH2:25]N>C(O)C.[Ni]>[OH-:23].[NH4+:13].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]=[C:12]([NH2:25])[C:11]23[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a turbid solution of 5′-(3-Chlorophenyl)-N-hydroxyspiro[cyclohexane-1,3-[3H]indol]-2-amine (0.500 g; 1.53 mmol) in 25 mL of ethanol was added hydrazine hydrate (0.600 mL; 12.24 mmol). The solution was warmed to 55° C., where Raney-nickel (50% in water) was added to the reaction to keep a constant evolution of gas. After 45 minutes, the hot reaction mixture was filtered through a Celite plug and rinsed with a copious amount of hot methanol. The filtrate was concentrated in vacuo to give 0.890 g of an opaque solid. The product was purified by flash silica gel chromatography; (eluant, 2% to 8% methanol-methylene chloride with 0.1% ammonium hydroxide) to afford 0.310 g (65%) of the desired product as a white solid. Mp. 118–120° C. 1H NMR δ (300 MHz, DMSO-d6) 1.31–1.46 (m, 2H), 1.70–1.93 (m, 8H), 7.0 (d, 1H), 7.1 (br, 2H, 2NH), 7.31–7.34 (dt, 1H, J=8 Hz), 7.41–7.46 (t, 2H), 7.55–7.58 (d, 1H), 7.62 (s, 1H), 7.72 (s, 1H); MS (ECI(+ve)) m/z 311 (M+H)+.

Workup

filtrationthe hot reaction mixture was filtered through a Celite plug
washrinsed with a copious amount of hot methanol
concentrationThe filtrate was concentrated in vacuo
customto give 0.890 g of an opaque solid
customThe product was purified by flash silica gel chromatography

Sources & evidence

ORD record: ord-a9e750599b754d7482e18a1d5914ad02
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091234B2

Reaction notes

Loading…