Triethylamine → HCID 23045036, compound

HRID 2108103Notes

Reaction equation

HRID 2108103 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CCCCCC.C(OCC)(=O)C.O.CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:24]3[CH2:23][CH2:22][N:21]([CH2:20][C:19]4[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:17]([O:16][CH3:15])[CH:18]=4)[CH2:26][CH2:25]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 23045036HCID 23045036, compoundYield 74.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of indole-5-carboxylic acid (1 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.2 g), triethylamine (1.9 g) and N,N-dimethylformamide (20 ml) is added dropwise under ice-cooling diethyl cyanophosphonate (1.5 ml), followed by stirring for 30 minutes under ice-cooling and for further one hour at room temperature. After addition of water (200 ml), ethyl acetate (200 ml) and hexane (50 ml), the reaction mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated. The residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1) to give 1-(5-indolylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine (1.9 g) as a colorless oily product. This product (0.3 g) is led to its fumarate in ethyl ether to obtain colorless powder (0.25 g).

Workup

  1. additionis added dropwise under ice-
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by means of a silica gel column chromatography(hexane:acetone=1:1)

Sources & evidence

ORD record
ord-5782f013af1c429581ea0bf0fd200b37
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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