Dimethylformamide → 3-(3-diethylaminopropyl)-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

HRID 24342Notes

Reaction equation

HRID 24342 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1([CH3:24])[CH2:15][C:14]2[NH:13][CH:12]=[C:11]([CH2:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[C:10]=2[CH2:9][CH2:8]1.CN([CH:28]=[O:29])C>>[CH2:20]([N:19]([CH2:22][CH3:23])[CH2:18][CH2:17][CH2:16][C:11]1[C:10]2[CH2:9][CH2:8][C:7]([CH3:6])([CH3:24])[CH2:15][C:14]=2[NH:13][C:12]=1[CH:28]=[O:29])[CH3:21]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 22571045[3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamine

Product 1

HCID 225710483-(3-diethylaminopropyl)-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Procedure

POCl3 (0.35 mL, 3.74 mmol) was added dropwise to DMF (0.8 mL, 10.3 mmol) at −5° C. After stirring at room temperature for 30 min, the mixture was cooled to −5° C. A solution of [3-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-diethylamine (0.9 g, 3.4 mmol) in DMF (2 mL) was then added dropwise. The mixture was stirred at room temperature for 3 hours and then quenched with ice, followed by 10 N KOH to adjust pH to 10-11. After stirring at room temperature for 1 hour, the mixture was extracted with EtOAc, washed with brine, dried and concentrated to give 0.55 g 3-(3-diethylaminopropyl)-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde.

Workup

  1. temperaturethe mixture was cooled to −5° C
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. customquenched with ice
  4. stirringAfter stirring at room temperature for 1 hour
  5. extractionthe mixture was extracted with EtOAc
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-906dad26d65840e0867e33d0e06fc984
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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