Water → HCID 69686798, compound

HRID 1532996Notes

Reaction equation

HRID 1532996 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17](I)[C:16]=3[O:22][CH2:23][CH3:24])[CH2:8]2)=[CH:4][CH:3]=1.[OH2:27].[CH3:28][N:29](C=[O:32])C>[C-]#N.[Zn+2].[C-]#N>[C:16]([OH:22])(=[O:32])[C:15]([OH:14])=[O:27].[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:28]#[N:29])=[CH:17][C:16]=3[O:22][CH2:23][CH3:24])[CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 22011794HCID 22011794, compound

Product 1

HCID 69686798HCID 69686798, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
80 °C

Procedure

A mixture of (±)-4-(4-chlorobenzyl)-2-[(2-ethoxy-iodophenoxy)methyl]-morpholine (1.0 g, 2.1 mmol), zinc cyanide (0.17 g, 1.4 mmol) and tetrakis(triphenylphosphino)palladium(O) (349 mg, 0.3 mmol) in DMF (15 ml) was heated to 80° C. for 3 h. Water was added and the solids were filtered off. The filtrate was extracted twice with ethyl acetate. Drying over magnesium sulfate was followed by evaporation. The crude product was dissolved in ether and an ethereal solution of oxalic acid was added to precipitate the product.

Workup

  1. filtrationthe solids were filtered off
  2. extractionThe filtrate was extracted twice with ethyl acetate
  3. dry with materialDrying over magnesium sulfate
  4. customwas followed by evaporation
  5. dissolutionThe crude product was dissolved in ether
  6. additionan ethereal solution of oxalic acid was added
  7. customto precipitate the product

Sources & evidence

ORD record
ord-fe65429694ee4b67ba00f8a45cb0aacb
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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