Potassium Carbonate → HCID 21939819, compound

HRID 1242875Notes

Reaction equation

HRID 1242875 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]4[CH:29]=[CH:28][C:24]([C:25]([O-])=[O:26])=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[NH2:35].C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])[O-].[K+].[K+]>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:30][O:31][C:32]1[CH:33]=[C:34]([NH:35][C:25](=[O:26])[C:24]2[CH:23]=[CH:22][C:21]([CH2:20][O:19][C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[CH2:10][CH:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:18][CH2:17]4)=[CH:29][CH:28]=2)[CH:36]=[CH:37][C:38]=1[O:39][CH3:40]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 757711-HydroxybenzotriazoleHCID 21939875HCID 21939875, compound

Product 1

HCID 21939819HCID 21939819, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

WSCD (free form, 0.2 ml) was added to DMF solution (3 ml) of 4-[[2-(2-piperidinoethyl)-6-tetralinyl]oxymethyl]benzoate (300 mg), 3,4-dimethoxyaniline (120 mg), HOBt (120 mg) and DMAP (100 mg) at room temperature, which was stirred for 12 hours. 10% aqueous potassium carbonate solution was added to the reaction mixture, and the resulting crystals were collected by filtration. The crystals were washed with water, then dried. The crystals were purified using alumina column chromatography (development solvent; THF), and recrystallized (THF-IPE) to give the titled compound (330 mg).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washThe crystals were washed with water
  3. customdried
  4. customThe crystals were purified
  5. customrecrystallized (THF-IPE)

Sources & evidence

ORD record
ord-eedada746ee04d9f8cc39615ccaf130f
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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