Diisopropylamine → HCID 23734890, compound

HRID 1042040Notes

Reaction equation

HRID 1042040 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C(NC(C)C)(C)C.[I:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.NCCN(CCN)CCN>ClCCl>[I:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 611632-MorpholinoethanolHCID 743734-Iodobenzoyl chlorideHCID 77731Tris(2-aminoethyl)amine

Product 1

HCID 23734890HCID 23734890, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 8 mL vial was charged with 2-morpholinoethanol (200 μL, 1.63 mmol), dichloromethane (5 mL), polystyrene-linked diisopropylamine (4.90 mmol), and 4-iodobenzoyl chloride (479 mg, 1.80 mmol), and the reaction mixture was shaken at room temperature. After 16 hours, the reaction mixture was charged with polystyrene-linked tris(2-aminoethyl)-amine (1.63 mmol), and shaken at room temperature for 2 hours. The reaction was filtered, and the resin was washed with dichloromethane (3×10 mL), tetrahydrofuran (2×10 mL), and diethyl ether (2×10 mL). The combined filtrates were concentrated in vacuo to give 2-morpholinoethyl 4-iodobenzoate (434 mg, 1.19 mmol) as a white solid.

Workup

  1. stirringshaken at room temperature for 2 hours
  2. filtrationThe reaction was filtered
  3. washthe resin was washed with dichloromethane (3×10 mL), tetrahydrofuran (2×10 mL), and diethyl ether (2×10 mL)
  4. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-cf4758afc33245cba93c640345e11def
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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