Morpholine → HCID 677187, compound

HRID 900553Notes

Reaction equation

HRID 900553 reaction equation
Br[CH2:2][C:3](Br)=[O:4].[I:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.CCN(CC)CC.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C1C=CC=CC=1.CCOC(C)=O>[I:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:3](=[O:4])[CH2:2][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 108934-IodoanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 677187HCID 677187, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromoacetyl bromide (175 L, μ2.00 mmol) was added dropwise over 5 minutes to a solution of 4-iodoaniline (438 mg, 2.00 mmol) and Et3N (280 μL, 2.00 mmol) in benzene (5 mL). The reaction was stirred 1 hour, treated with morpholine (1.0 mL, 11.5 mmol) and stirred overnight. The reaction mixture was diluted with EtOAc (200 mL), washed with aqueous 0.1 M KOH (50 mL), H2O (50 mL), dried over MgSO4 and concentrated to give a yellow oil. Purification by silica gel chromatography (100:1 CH2Cl2/MeOH) afforded 630 mg (91%) of N-(4-iodophenyl)-2-morpholin-4-ylacetamide as a waxy tan solid. This product was converted to analogues in a similar manner as Example 14.

Workup

  1. stirringstirred overnight
  2. washwashed with aqueous 0.1 M KOH (50 mL), H2O (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customPurification by silica gel chromatography (100:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-3984ed4dbc074696b6390aac572ee876
Source dataset
uspto-grants-2008_04
Patent number
US07358359B2

Reaction notes

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