Morpholine → N-[8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholine

HRID 2268446Notes

Reaction equation

HRID 2268446 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](O)=[O:31])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH2:7]1)=[O:5])[CH3:2].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:31])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

Product 1

HCID 18348513N-[8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholineYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF (4.0 ml) suspension of 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (114 mg, 0.252 mmols), morpholine (0.110 ml, 1.26 mmols), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (96.6 mg, 0.504 mmols) and 1-hydroxybenzotriazole monohydrate (77.2 mg, 0.504 mmols) was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, to which was added water. Then, this was extracted with ethyl acetate, and the organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1) to obtain the entitled compound (123 mg) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, to which
  2. additionwas added water
  3. extractionThen, this was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out
  7. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-fb77886e38dc4c1b901b16b38b7d8bc8
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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