Triethylamine → N-Methyl-2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxamide

HRID 2268450Notes

Reaction equation

HRID 2268450 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([C:27]([OH:29])=O)[CH2:18][C:17]2[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=2[O:19][CH3:20])[CH2:11]1.[Cl-].C[NH3+].Cl.[CH2:34]([N:36]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1>[CH3:34][NH:36][C:27]([C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[CH2:18][C:17]2[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=2[O:19][CH3:20])[CH2:11]1)=[O:29]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11637Methanamine, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183485542-(8-Hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxylic acid

Product 1

HCID 18348606N-Methyl-2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indancarboxamideYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF (3.0 ml) solution of 2-(8-hydroxyoctyl)-4,5,6,7-tetramethoxy-2-indan-carboxylic acid (300 mg, 0.731 mmols) was added to a THF (3.0 ml) suspension of methyl ammonium chloride (247 mg, 3.66 nmnols), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (420 mg, 2.19 mmols), 1-hydroxybenzotriazole monohydrate (335 mg, 2.19 mmols) and triethylamine (1.02 ml, 7.31 mmols), at room temperature. The reaction mixture was stirred for 12 hours, and then concentrated in vacuo. Water was added to the resulting residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by alumina column chromatography (ethyl acetate) to obtain the entitled compound (277 mg) as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater was added to the resulting residue, which
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by alumina column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-57cd8f0bee1c49d5acad01e3eec22b57
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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