Dimethylformamide → 3-[3-(4-Methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde
Reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[NH:18][CH:17]=2)[CH2:9][CH2:8]1.CN(C)[CH:27]=[O:28]>>[CH3:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[NH:18][C:17]=2[CH:27]=[O:28])[CH2:11][CH2:12]1Participants
Conditions
- Temperature
- -5 °C
Procedure
POCl3 (1.8 mL, 18.9 mmol) was added dropwise to N,N-dimethylformamide (DMF, 3.8 mL, 51.6 mmol) at −5° C. The mixture was then allowed to come to room temperature and then stirred for 30 minutes after which it was again cooled to −5° C. A solution of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole (4.5 g, 17.2 mmol) in DMF (9 mL) was added dropwise. The mixture was again allowed to come to room temperature and then stirred at that temperature overnight. The reaction was then quenched with ice, followed by 10 N NaOH to adjust the pH to 10-11. After stirring at room temperature for 1 hr, the reaction was extracted with ethyl acetate (EtOAc), the organic layer separated, washed with brine, dried and concentrated to give 3.1 g (62%) of 3-[3-(4-methylpiperazin-1-yl)-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde.
Workup
- customto come to room temperature
- customto come to room temperature
- stirringstirred at that temperature overnight
- customThe reaction was then quenched with ice
- stirringAfter stirring at room temperature for 1 hr
- extractionthe reaction was extracted with ethyl acetate (EtOAc)
- customthe organic layer separated
- washwashed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fedb7d0809d3478fa5c4191038520985
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855730B2
Reaction notes
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