Trimethylsilyl triflate → N,N-dimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine
Reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH3:13][N:14]([CH3:40])[C:15]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:20][CH2:19][C:18]([CH2:22][CH2:23][CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)(O)[CH2:17][CH2:16]1>ClCCl>[CH3:13][N:14]([CH3:40])[C:15]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:20][CH2:19][C:18]2([C:26]3[NH:27][C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]=3[CH2:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1Participants
Procedure
Trifluoromethane sulphonic acid trimethylsilyl ester (755 mg, 617 μL, 3.4 mmol) was added to a suspension of 4-dimethylamino-1-[3-(1H-indol-3-yl)propyl]-4-phenylcyclohexanol (320 mg, 0.85 mmol) in absolute dichloromethane (20 mL), wherein a clear brown solution formed that was stirred for 14 d at room temperature. The reaction solution was then diluted with dichloromethane (10 mL), washed with 1 N sodium carbonate solution (2×10 mL), water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (270 mg) was mixed with methanol (30 mL) and stirred overnight at room temperature, wherein a light-coloured solid formed, which was filtered off and washed with a little methanol (2 mL).
Workup
- customformed
- washwashed with 1 N sodium carbonate solution (2×10 mL), water and saturated sodium chloride solution (10 mL each)
- dry with materialdried with sodium sulphate
- concentrationconcentrated to low volume in a vacuum
- additionThe residue (270 mg) was mixed with methanol (30 mL)
- stirringstirred overnight at room temperature
- customwherein a light-coloured solid formed
- filtrationwhich was filtered off
- washwashed with a little methanol (2 mL)
Sources & evidence
- ORD record
- ord-5a7e2eedbb9b4469a8fb87633fb64698
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288430B2
Reaction notes
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