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

HRID 1372384Notes

Reaction equation

HRID 1372384 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 10 g (60.8 mmol) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid in 60 mL of dichloromethane was added 11.6 gm (71.8 mmol) of 1,1′-carbonyldiimidazole followed by 5.5 mL (60.8 mmol) of morpholine and 10 mL (60.8 mmol) of N,N-diisopropylethylamine. The dark red reaction mixture was stirred at room temperature overnight and poured into ice water. The organic layer was washed with brine until its pH was 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% yield) 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 its pH was 6
  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-14a7ac5f8a374025b246e86af8aaf613
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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