Triethylamine → HCID 86588562, compound

HRID 1836135Notes

Reaction equation

HRID 1836135 reaction equation
C(N(CC)CC)C.[N:8]1([CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][C:18]=2[CH:26]=[O:27])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30].ClCCl.CO>CN(C)C=O>[CH2:32]([O:31][C:29]([N:11]1[CH2:12][CH2:13][N:8]([CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][C:18]=2[CH:26]=[O:27])[CH2:9][CH2:10]1)=[O:30])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21226129Dichloromethane methanolHCID 234988213-(3-piperazin-1-yl-propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Product 1

HCID 86588562HCID 86588562, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (146 μl, 1.0 mmol) was added to 3-(3-piperazin-1-yl-propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (192 mg, 0.7 mmol) in 5 ml of dimethylformamide at 0° C. Ethyl chloroformate (87 μl, 0.91 mmol) was dropped in the mixture. The reaction mixture was stirred at 0° C. which was raised slowly to room temperature over night. Thin layer chromatography (dichloromethane: methanol 10:1) showed on major spot. The solvent was evaporated then the residue was purified by flash chromatography and eluting with (dichloromethane/methanol =50/1, 40/1, 30/1) to give 130 mg of 4-[3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propyl]-piperazine-1-carboxylic acid ethyl ester.

Workup

  1. temperaturewas raised slowly to room temperature over night
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography
  4. washeluting with (dichloromethane/methanol =50/1, 40/1, 30/1)

Sources & evidence

ORD record
ord-d1f5766a8f8c446bb781e18a218dbf11
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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