Morpholine → 4-[(4-Iodophenyl)carbonyl]morpholine

HRID 2410745Notes

Reaction equation

HRID 2410745 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[I:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1>C1COCC1.C(Cl)Cl>[I:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:36])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 120854-Iodobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 7726344-[(4-Iodophenyl)carbonyl]morpholineYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (12.1 g, 62.9 mmol), 1-hydroxybenzotriazole hydrate (9.63 g, 62.9 mmol), and morpholine (9.13 g, 105 mmol) was added to a solution of 4-iodobenzoic acid (13 g, 52.4 mmol) in a mixture of THF (250 mL) and methylene chloride (50 mL). After stirred at 25° C. for 20 hr, the solvent was removed and flash silica gel chromatography (step gradient elution with methylene chloride containing 0 to 3% MeOH) afforded (4-iodophenyl)(morpholino)-methanone (15.1 g). MS (ESI) m/z 317.9 (M+H). 1H NMR (CDCl3) δ ppm 7.76 (2H, d, J=8.24 Hz), 7.14 (2H, d, J=8.24 Hz), 3.23-4.00 (8H, m).

Workup

  1. customthe solvent was removed
  2. washflash silica gel chromatography (step gradient elution with methylene chloride containing 0 to 3% MeOH)

Sources & evidence

ORD record
ord-bb5ce0b412a441e3a443778b84ac957f
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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