Hydrochloric Acid → HCID 67094298, compound

HRID 1881203Notes

Reaction equation

HRID 1881203 reaction equation
Cl[C:2]1[C:3]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8].[CH3:23][Al](C)C.C(O)C.Cl>COCCOC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:4]2[S:5][C:6]([C:7]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[O:8])=[C:2]([CH3:23])[C:3]=2[CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 16682925TrimethylaluminumHCID 67094295HCID 67094295, compound

Product 1

HCID 67094298HCID 67094298, compound

Reagents, catalysts & solvents 3

HCID 178418745HCID 178418745, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(3-Chloro-5,6-dimethoxybenzo[b]thiophen-2-yl)morpholin-4-yl-methanone (3.0 g) from Example 8, trimethylaluminum (3.2 g) and [1,3-bis(diphenylphosphino)propane]dichloronickel (II) (1.2 g) in 1,2-dimethoxyethane (100 ml) were refluxed under argon for 10 hours. To the cold mixture ethanol (50 ml), water and HCl were added respectively and the mixture was extracted with ethyl acetate. Ethyl acetate was dried and evaporated to dryness. The crude product was purified by flash chromatography eluting with heptane-ethyl acetate (5:5).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialEthyl acetate was dried
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography
  5. washeluting with heptane-ethyl acetate (5:5)

Sources & evidence

ORD record
ord-421006376ca44861999aea27c3b0fa67
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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