Sodium Iodide → 1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2-morpholin-4-yl-ethyl)-[1,4]diazepan-5-one

HRID 1867406Notes

Reaction equation

HRID 1867406 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([C:12](=[O:22])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[CH2:6][CH2:5]1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[Na+].[I-]>CC(N(C)C)=O>[Cl:21][C:17]1[CH:16]=[C:15](/[CH:14]=[CH:13]/[C:12]([N:7]2[CH2:8][CH2:9][C:10](=[O:11])[N:4]([CH2:3][CH2:2][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH2:5][CH2:6]2)=[O:22])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 684323164-(2-Chloro-ethyl)-1-[(E)-3-(3-chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

Product 1

HCID 684342551-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2-morpholin-4-yl-ethyl)-[1,4]diazepan-5-oneYield 8.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 0.085 g (0.25 mmol) of 4-(2-chloro-ethyl)-1-[(E)-3-(3-chloro-phenyl)-acryloyl]-[1,4]diazepan-5-one in 1.3 ml of DMA was treated with 0.04 ml (0.50 mmol) of morpholine and stirred for 8 h at RT, a crystal of NaI was added and stirring was continued for 40 h. The reaction was extracted with aqueous saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4), concentrated and evaporated. Purification by catridges, Si-Amine, 70 ml, 20 g (EtOAc) gave 0.008 g (8%) of the title compound as off-white viscous oil. MS: 392.0 (MH+, Cl).

Workup

  1. stirringstirring
  2. waitwas continued for 40 h
  3. extractionThe reaction was extracted with aqueous saturated NaHCO3/EtOAc (3×)
  4. washThe organic phases were washed with aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customevaporated
  8. customPurification by catridges, Si-Amine, 70 ml, 20 g (EtOAc)

Sources & evidence

ORD record
ord-dc1f02649b454e338c77715b26337b5a
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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