Aniline → 2'-Methylspiro[cyclohexane-1,3'-indole]

HRID 985713Notes

Reaction equation

HRID 985713 reaction equation
[C:1]([C:3]1(O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.NC1C=CC=CC=1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Ru].[Ru].[Ru].ClCCl>[CH3:2][C:1]1[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 65251-EthynylcyclohexanolHCID 8870Benzenamine hydrochloride (1:1)

Product 1

HCID 3391132'-Methylspiro[cyclohexane-1,3'-indole]Yield 1.2%

Reagents, catalysts & solvents 2

HCID 6096991Triruthenium dodecacarbonylCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

1-Ethynyl-1-cyclohexanol (1.242 g, 10 mmol), aniline (0.931 g, 10 mmol), Ru3(CO)12 (32.0 mg, 0.05 mmol) and aniline hydrochloride (0.259 g, 2.0 mmol) were placed in a 10 ml round-bottomed flask, and the mixture was stirred at 120° C. for 12 hours. After cooling, dichloromethane (3 mL) was added, and the organic layer was washed twice with 1 M hydrochloric acid (2 mL) and once with water (2 mL). The organic layer was dried over sodium sulfate, and the solvent was distilled away, whereby 2-methyl-3H-indole-3-spiro-1′-cyclohexane (24 mg; 0.12 mmol; yield, 1.2%; purity, 95% or more) was obtained.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed twice with 1 M hydrochloric acid (2 mL) and once with water (2 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-5ecff62f5d9440c1ab9b52585fc1ae23
Source dataset
uspto-grants-2005_03
Patent number
US06872835B2

Reaction notes

Loading…