Tetrahydrofuran → Ethyl 4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-1-(1-oxododecyl)-2-piperazine acetate

HRID 476882

Reaction equation

HRID 476882 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]2=[O:24])=[CH:2]1.C(N(CC)CC)C.[CH2:32](Cl)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].[O:45]1CCCC1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:32](=[O:45])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:14]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]2=[O:24])=[CH:2]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81921-ChlorododecaneHCID 8471TriethylamineHCID 14257258Ethyl 4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-2-piperazine acetate

Product 1

HCID 70378265Ethyl 4-[2-(1H-indol-3-yl)-ethyl]-3-oxo-1-(1-oxododecyl)-2-piperazine acetate

Procedure

2.14 g of the product of Step C of Example 1 were dissolved in a mixture containing 1.4 ml of triethylamine and 25 ml of tetrahydrofuran. 1.5 ml of lauryl chloride were added dropwise and after stirring for 30 minutes, the precipitate was filtered off. The filtrate was concentrated to dryness and the residue was taken up in methylene chloride, washed with water and dried. The solvent was eliminated under reduced pressure at 50° C. to obtain 3.2 g of the expected product.

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationThe filtrate was concentrated to dryness
  3. washwashed with water
  4. customdried
  5. customwas eliminated under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-bd0dc14117b6432784458830487d75c4
Source dataset
uspto-grants-1989_12
Patent number
US04886802

Linked notes

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