Morpholine → 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one

HRID 1815429Notes

Reaction equation

HRID 1815429 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:12])[C:6]=1[CH2:7][CH2:8][C:9]([OH:11])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:12])[C:6]=1[CH2:7][CH2:8][C:9]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:11]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 15125193-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

Product 1

HCID 219257553-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-oneYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (10 g, 60.8 mmol) in 60 ml of dichloromethane was added 1,1′-carbonyldiimidazole (11.6 g, 71.8 mmol) followed morpholine (5.5 ml, 60.8 mmol) and N,N-diisopropylethylamine (Hunig's base, 10 ml, 60.8 mmol). The dark red reaction mixture was stirred at room temperature overnight and poured into ice water. The organic layer was washed with brine until the wash had a pH of about 6, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified on a silica gel column eluting with dichloromethane-methanol (98:2) to give 13.84 g (96%) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one.

Workup

  1. customThe dark red reaction mixture
  2. washThe organic layer was washed with brine until the wash
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column
  6. washeluting with dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-0552ef97ecb443c5a0c1deea74d14920
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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