Triethylamine → 1-Benzyl-4-(2-indolylacetamido)piperazine

HRID 2395266Notes

Reaction equation

HRID 2395266 reaction equation
O[N:2]1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[CH2:27][C:28]([OH:30])=O.[CH2:31]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.CN(C)CCCN=C=NCC>C1COCC1>[CH2:31]([N:38]1[CH2:43][CH2:42][N:41]([NH:2][C:28](=[O:30])[CH2:27][C:19]2[NH:18][C:26]3[C:21]([CH:20]=2)=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:40][CH2:39]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43717522-Indolylacetic acid

Product 1

HCID 189716181-Benzyl-4-(2-indolylacetamido)piperazineYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxybenzotriazole (324 mg, 2.4 mmol) and triethylamine (446 μl, 3.2 mmol) were added to a solution of indole-2-acetic acid (350 mg, 2 mmol) and 1-benzylpiperazine (352 mg, 2 mmol) in THF (25 ml), followed after 5 min by 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (576 mg, 3 mmol) and the mixture stirred for 15 h. The mixture was concentrated in vacuo and the residue partitioned between citric acid (1M, 30 ml) and ethyl acetate (25 ml), the phases were separated and the aqueous layer extracted with ethyl acetate (2×25 ml). The combined organic layers were washed with sodium bicarbonate (satd., 2×10 ml) and brine (satd., 20 ml), dried (Na2SO4) and evaporated in vacuo to give 1-benzyl-4-(2-indolylacetamido)piperazine as a pink solid (200 mg, 30%), m/z (CI+, NH3) 334 (M+1)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between citric acid (1M, 30 ml) and ethyl acetate (25 ml)
  3. customthe phases were separated
  4. extractionthe aqueous layer extracted with ethyl acetate (2×25 ml)
  5. washThe combined organic layers were washed with sodium bicarbonate (satd., 2×10 ml) and brine (satd., 20 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2c61e4c9a77a4615b9ef1dd501028a72
Source dataset
uspto-grants-1998_09
Patent number
US05814644

Reaction notes

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