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

HRID 230630Notes

Reaction equation

HRID 230630 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>ClCCl>[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 7726344-[(4-Iodophenyl)carbonyl]morpholineYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of morpholine (653 mg, 7.5 mmol) in dichloromethane (40 ml) was cooled in an ice/methanol bath and then treated with stirring under argon with triethylamine (7.5 mmol, 1.05 ml) followed by the portionwise addition of 4-iodobenzoyl chloride (2.0 g, 7.5 mmol). The reaction mix was allowed to stir at room temperature for 0.5 h before the solution was washed with water (2×20 ml). The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a yellow solid (2.4 g, 100%).

Workup

  1. additiontreated
  2. additionThe reaction mix
  3. washwas washed with water (2×20 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b746e00f5e2543e68206f527e7503502
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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